AI transcript
0:00:04 If you’re a young man in your 20s and 30s, and you want to be more confident, this episode
0:00:05 is for you.
0:00:06 And it’s going to be a little strange.
0:00:09 If you saw this headline, if you saw this title, you’re going to think, why on earth
0:00:11 is this happening on a business podcast?
0:00:13 Today’s episode is with Die Workwear.
0:00:18 Die Workwear is the username of a person who’s gone incredibly viral on Twitter.
0:00:21 He has over a million followers, and he talks about men’s fashion.
0:00:26 I saw this guy pop up last year, and it kind of changed my life because he taught me about
0:00:31 dress and how dressing a certain way, it gives a huge amount of confidence.
0:00:36 And the problem is that you don’t try to dress nice because you don’t really know the rules.
0:00:40 And so I thought it’d be fun to talk to Derrick about his rise, so how he got huge and built
0:00:45 the business, but also some practical tips on how to dress better and what that means
0:00:47 for your life and what that means for your confidence.
0:00:50 So give this episode a listen, and I’ll talk to you in a little bit.
0:01:02 I think the reason why you’re blowing up right now, I’ll give you my opinion, and maybe
0:01:04 you could give me your opinion.
0:01:09 But I care how I look, and I’ve always cared about that, but I never really knew the rules.
0:01:13 And basically, when you don’t know the rules of something, you feel not confident and you
0:01:16 kind of just revert back to like, well, I’m just going to do the lazy thing of like wearing
0:01:20 athleisure or like kind of boring clothes.
0:01:25 But you have this line that you repeat constantly, which is clothing is a social language.
0:01:29 And you kind of have taught people how to speak it, which kind of gives confidence.
0:01:34 And it makes your clothing feel like armor, but also you’re dressing like the person you
0:01:35 want to be.
0:01:38 And you’re speaking the language of the people who you want to speak with and kind of what
0:01:40 you want to behave like.
0:01:43 And I think this is why millions of men have liked you because you’re giving them confidence
0:01:45 and teaching them the language.
0:01:48 I do think of clothing as social language.
0:01:53 And I’ve always thought of it in that sense because, you know, if you grew up anytime
0:01:58 before the internet, you know, you may have been part of some social group around a hobby
0:02:03 or an interest like you were a skater or you’re into punk music or whatever.
0:02:07 And everyone I knew dressed a certain way to communicate an identity like they were
0:02:09 a jock or they were a nerd or whatever.
0:02:13 And there was always rules around that look, even if no one wrote a book and spelled it
0:02:14 out for you.
0:02:17 Everyone kind of knew that this was the look.
0:02:20 And everyone kind of conformed to the look of their social group and identity, and they
0:02:23 kind of broadcasted a message.
0:02:29 And I think over time, I’ve just kind of taken that idea and talked about how it’s also
0:02:35 used in classic tailoring or, you know, tech wear or whatever is the aesthetic genre.
0:02:37 People are using dress to communicate something.
0:02:43 And even people who dress in ways that is subconscious that they think they don’t care
0:02:48 about clothes, they still kind of dress according to their socio-economic class.
0:02:50 I bring up this example often.
0:02:55 There was a moment in the tech industry in the early 2000s where the hoodies and jeans
0:02:59 uniform was a way to signal, I don’t care about clothes.
0:03:04 I’m like the whiz kid, you know, kind of hacker that’s reshaping the economy.
0:03:07 All I care is about meritocracy and skills.
0:03:10 But it just so happens that over time within that industry, everyone started to also dress
0:03:11 the same.
0:03:16 So to some degree, people are at least conscious of what is the look within their group.
0:03:21 And they were careful to not deviate too far from it because they want to signal that
0:03:22 they belong.
0:03:26 There’s a there’s an article that I often mention on Twitter and sometimes in interviews.
0:03:28 The author’s name is Carlos, but I can’t remember his last name.
0:03:33 But he wrote an article called inside the meritocracy mirror, like looking into the
0:03:34 mirror and then talk.
0:03:38 And in his article was about how even in the tech industry where people say they don’t
0:03:42 care about clothes, everyone mirrors each other.
0:03:47 And clothes do play a part because if you showed up to a job interview for the tech
0:03:51 industry and you wore a three piece suit, people assume that you don’t fit in and they
0:03:53 will read something into your clothes.
0:03:55 So to some degree, clothes do matter.
0:03:59 Hey, let’s take a quick break.
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0:04:39 This is the first time we’ve ever done an anonymous podcast and I want to ask you about
0:04:40 your rise.
0:04:43 So if there’s ever anything that you just don’t want to answer, just let me know.
0:04:48 But is this your full-time gig now, which is kind of being a writer or whatever it is
0:04:50 you describe yourself as?
0:04:54 Yeah, I make my living off writing about menswear.
0:04:59 There’s this concept that I think I learned from you or a rabbit hole you sent me down.
0:05:04 Is it called a sprezzatura where it’s like you’re being careless, but that’s kind of
0:05:05 the cool part, right?
0:05:07 It’s like not trying too hard, but you look amazing.
0:05:09 Did I explain that accurately?
0:05:15 Yes, it was originally introduced by an Italian writer during the 16th, 17th century.
0:05:23 And the writer who originally used this term was describing how to serve the king.
0:05:28 And they were saying that you should do things in a way that conceals your effort.
0:05:34 An easy way to understand this is like if Sam asked me to do a favor, can you pick up
0:05:38 my car from this location and drive it to this place?
0:05:41 I will do the favor, but insist that it’s no big deal.
0:05:42 It’s not a problem.
0:05:43 Don’t worry about it.
0:05:50 Even if it is actually kind of inconvenient, and it’s a way to essentially, I guess serve
0:05:55 you, is to make the person feel good about what they’ve asked of you.
0:06:03 The sprezzatura in a men’s style sense is basically to dress in a way that conceals the effort
0:06:05 that you’ve put in.
0:06:08 But the concept goes way back before this writer.
0:06:14 It goes back to even Brummel, who is largely understood to have shaped much of moderns
0:06:15 men’s style.
0:06:21 And Brummel used to spend hours tying his cravat, his white cravat, which is kind of
0:06:22 like a necrochiff.
0:06:28 This is a famous story, probably made up, but the story is that one of his valets was
0:06:33 seen exiting the room once with a huge pile of cravats, and someone asked him, “What are
0:06:34 those for?”
0:06:37 And he said, “These are our failures.”
0:06:41 And the idea was that Brummel actually spent hours and hours and hours in the morning putting
0:06:42 together his look.
0:06:46 And then he’d walk out and then pretend that he just happened to have fell into these clothes.
0:06:48 Like it was no big deal.
0:06:50 It was a complete natural thing.
0:06:52 He woke up like this.
0:06:56 And that is part of the idea that style is kind of a natural extension of you, and it’s
0:06:58 not an artifice.
0:07:02 And that’s sort of, you’re doing Spresitaro with your Twitter handle and with your writing
0:07:03 and with your reach.
0:07:07 You’re like, “Oh, I just kind of just wrote what came interesting.
0:07:14 And I don’t know how big it is, but in reality, you’re just behind the scenes just scheming.
0:07:19 You’re just, you’re like, “Oh, I just wrote this really funny burn to this guy who replied.”
0:07:23 And it just happened to get 2 million views because that’s one of the things that you
0:07:29 do, which is pretty funny, is you reply to a couple of people, but you murder them.
0:07:30 It’s called murdered with words.
0:07:34 You just kind of annihilate them.
0:07:37 And that’s kind of your style, which I find hilarious.
0:07:41 But one person you’ve turned me onto is Ralph Lauren.
0:07:45 And Ralph Lauren has an interesting story, but I’m like getting obsessed with some of
0:07:49 his quotes because he was raised a very normal background.
0:07:52 But he said that he got obsessed with movies at a young age.
0:07:57 He was like, I’m not sure if I can be an actor, but I can design my life via clothing.
0:08:00 If I put on a farmer’s outfit, I’ll feel like a farmer.
0:08:03 If I put on a soldier style office, I’m going to feel like a soldier.
0:08:04 I’ll feel tough and brave.
0:08:05 And he has this great quote.
0:08:07 He says, “I don’t design clothes.
0:08:12 I design dreams.” And then he dresses as if whatever he wants to become.
0:08:14 He was a Jewish kid from the Bronx.
0:08:17 He was like, I want to feel like this old money sophistication.
0:08:19 So we started dressing like that and he became it.
0:08:23 And I think that’s what is interesting about what you’ve opened up to a lot of people is
0:08:26 this idea of acting as if and then you become.
0:08:27 Yeah.
0:08:30 If you go through a Ralph Lauren flagship, it’s not true for the normal stores.
0:08:33 The normal stores are just normal stores, but if you visit a Ralph Lauren flagship,
0:08:37 it’s like walking through like Epcot Center, like the amusement parks and there’s like
0:08:40 the pirate ship world and there’s a rocket ship world and all that.
0:08:43 You go through a Ralph Lauren flagship, there’s like the ranch world.
0:08:45 There’s the old money world.
0:08:48 There’s, you know, there’s all these different worlds that he creates around costumes.
0:08:54 And it’s because he knows how to imbue you with both that fantasy and to kind of use
0:09:00 that language and design to reference different social ideas and identities.
0:09:03 I want to ask you practical tips on like dress and things like that.
0:09:07 But I actually want to ask you practical tips first on learning.
0:09:09 I’ve noticed that you’re pretty insane.
0:09:14 Like I read a blog where it starts off like saying in the 1959 book, try for elegance,
0:09:16 which enters around men’s clothing.
0:09:19 And then you like quote the book and you tell a story about the book and that leads into
0:09:20 the rest of your writing.
0:09:22 I went and tried to find that book.
0:09:25 That was a book that’s out of print.
0:09:29 That’s like $300 or something like that and it has like no reviews on Amazon.
0:09:33 And then you’ll do like the history of tweed.
0:09:36 And I’m like, how the hell do you know this shit?
0:09:40 And so what I want to know is how are you learning all of these things and storing the
0:09:41 knowledge?
0:09:46 That’s what fascinates me about you is like your mastery of a topic.
0:09:50 That comes with a lot of buying stuff that ends up being crappy.
0:09:54 So I’ve bought a lot of books on clothing.
0:09:58 If they’re, you know, especially old books and if it was published in some, you know,
0:10:01 some time, you know, this obscure book I’d buy and then read it and a lot of that stuff
0:10:03 ends up being crappy.
0:10:05 But sometimes there’s like a nugget over time.
0:10:08 I think you get a better sense of like, which books to buy obviously you’re not just constantly
0:10:12 doing the scattershot, but I do end up buying a lot of books and then reading them.
0:10:15 And then sometimes there’s like a nugget here and there.
0:10:16 It does help.
0:10:22 I would say that fashion as a topic for a while was not treated seriously.
0:10:27 And then to the degree it is treated seriously, it’s often focused on women’s clothing.
0:10:34 And then to the degree that men’s clothing is taken seriously, there are many brilliant
0:10:39 academic writers who focus on men’s clothing, but they tend to be extremely academic.
0:10:47 So I am in a space where I’m just enthusiast and I try to write something that ties clothing
0:10:53 into other parts of culture, which I hope makes it more interesting to everyday people.
0:10:56 And I try to do something that’s a little bit smarter than just like basic trend reporting
0:11:00 or fashion writing, but it’s a little bit more accessible than academic writing.
0:11:03 And then I also tread this water where not a lot of people are treading.
0:11:05 And I think that kind of helps.
0:11:09 I think it helps to be in this very specific space.
0:11:16 Today you had a thing about like the quarter zip and like that caused so much, so much outrage.
0:11:19 And I think I said you were coming on, I got so many people that are pissed off that you
0:11:25 were coming because they were like, dude, he’s so unrelatable to the middle America guy.
0:11:28 And I think though that oddly those people are folks that are being turned on to you
0:11:29 right now.
0:11:33 What are the common issues that they come to you with?
0:11:37 And what’s the general advice to the three most common things for like, if you do this,
0:11:42 this and this, you’re going to be 60% of the way there or significantly better.
0:11:45 You can’t answer any of those things without first thinking of closed social language and
0:11:48 the thinking of what you want to communicate.
0:11:52 So if you think of closed social language, you are to me like 90% of the way there because
0:11:55 then you can think of like how something should fit and the colors and the styles and all
0:11:57 that to combine.
0:12:01 I admit that as my account has grown, I’ve leaned a little bit more towards tailoring.
0:12:05 Before my account started grow, I talked about a much wider range of styles, often like Japanese
0:12:06 workwear or something.
0:12:11 And I’ve leaned a little bit more into tailoring because that’s an aesthetic language that
0:12:12 I think more people understand.
0:12:14 Is that limited to suits?
0:12:19 Good sport coats, anything that would be considered like maybe smart casuals.
0:12:22 I think there are certain kind of aesthetics that like everyone recognizes, oh, that’s
0:12:23 good.
0:12:25 Again, bringing it back to language.
0:12:30 If you think of like dialects, received pronunciation, everyone recognizes that as like the quote
0:12:34 unquote correct pronunciation.
0:12:36 And they recognize that as the good English.
0:12:39 But you know, throughout the UK, there are many dialects.
0:12:44 And even though everyone recognizes received pronunciation as the dialect.
0:12:49 If you speak received pronunciation in certain parts of England, you might come off as kind
0:12:54 of crazy because everyone there speaks in a different dialect.
0:12:59 But if you take that dialect and put it across the nation, a lot of people are going to be
0:13:03 very opinionated on whether or not that is the correct way of speaking because that’s
0:13:04 very regional.
0:13:10 So there are certain modes of communication that are hegemonic and suit sport coats, but
0:13:15 a certain kind of like dressy kind of look is what I would consider hegemonic and visual
0:13:17 aesthetics.
0:13:24 Even though wearing a chore coat or wearing a punk rock biker jacket or other aesthetics
0:13:29 can be legitimate in their own way, it’s just that if you present that to other people,
0:13:34 it’s more controversial and fewer people are going to recognize it as quote unquote good
0:13:35 because it’s so regional.
0:13:40 The problem with I will admit when you talk about like the Midwestern guy, I get this a
0:13:46 lot is that somebody from outside of San Francisco or New York City or Los Angeles to say, “I
0:13:48 really like what you put out there.
0:13:50 How can I dress like this?”
0:13:57 And that is sometimes a question I can’t answer because if you want to wear sport coats and
0:14:03 you live outside of a handful of cities, and especially if you’re fall outside of straight
0:14:08 sizing, let’s say you’re a size 46 chest, I just got an email the other day, someone has
0:14:13 a 48 chest, but a 32 waist, so they’re a professional baseball player.
0:14:19 If you’re that build and you are outside of the major cities, I don’t really have an answer
0:14:23 for you because tailoring has died over the last few decades.
0:14:24 There aren’t many good tailors.
0:14:28 So what you’re going to find is a lot of ready to wear tailoring, which is not going to fit
0:14:30 an unusual build.
0:14:34 And then you also have to be the kind of guy that’s willing to wear a sport coat, even
0:14:37 though other people aren’t wearing a sport coat.
0:14:42 You have to put up with the fact that you are overdressed and you’re doing it for yourself
0:14:44 and it’s pleasing to you.
0:14:49 So sometimes if you’re in a smaller city, there may not be a lot of options and there
0:14:53 may be, I think, harsher judgments.
0:14:58 Whereas I think in a big city, you have a certain kind of anonymity where you can dress very
0:15:01 different from others and nobody cares.
0:15:06 Like nobody cares if you arrive to the office in a sport coat and everyone’s dressed down.
0:15:08 I’d still think you can in a small city.
0:15:11 I have a friend who works for a religious organization.
0:15:13 He lives just outside of Nashville.
0:15:15 Yeah, men musing.
0:15:16 Gentlemen musing.
0:15:18 Yeah, men’s wear musings.
0:15:19 Mitchell.
0:15:20 Yeah.
0:15:26 He works for a religious organization and he wears a sport coat with jeans to the office.
0:15:30 He told me that nobody in his office wears tailor clothing except for the really old
0:15:31 guys.
0:15:34 But he does it so often now that that’s just like him.
0:15:39 And one, he’s obviously not going to get fired for it, but two, it’s not like anyone comments
0:15:40 on it anymore.
0:15:41 It’s just him.
0:15:45 And I think it does take that kind of personality and it takes a willingness to really hunt
0:15:51 for those ready to wear pieces to figure out how things fit because historically, men dressed
0:15:56 well in tailored clothing, not because they knew all of this stuff, it’s because they
0:16:00 went to a local clotheir and that clotheir like outfitted them.
0:16:04 They, you know, you go to your clotheir and you’d say, I have to go to a summer wedding
0:16:08 or I work in this office, like just figure out how am I supposed to dress and that clotheir
0:16:10 told you, you’re going to summer wedding.
0:16:12 This is the thing that you’re supposed to wear and they’d figure out how it’s supposed
0:16:16 to fit and they do all the tailoring and all that and you walk out and you look amazing.
0:16:21 Those clothes have disappeared and customer loyalty is no longer there as well.
0:16:27 So whereas a man used to go to his tailor and would introduce his son to his tailor.
0:16:33 Now men shot from different places, not only different aesthetics, but they might buy their
0:16:37 jeans from a jean company shirts from a shirt company socks from a sock company.
0:16:42 Sometimes they’re also buying the stuff online where there’s no sales associate to guide them
0:16:47 and then they have to figure out how to put together not only a good outfit, but also
0:16:52 a good wardrobe and how to use that wardrobe to move throughout different social spaces.
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0:17:46 All right, you’re telling me this and I’m like, all right, I’m bought into all that,
0:17:47 but I feel hopeless.
0:17:49 So I live right outside New York City.
0:17:50 So it’s okay for me.
0:17:54 I can go to New York City, but I still feel hopeless where I’m like, this sounds super
0:17:55 intimidating finding a tailor.
0:17:56 Yeah.
0:17:59 There are solutions depending, everyone has to figure out their own specific situation.
0:18:04 If you’re the guy that emailed me recently, he’s a baseball player, 48 chest, 32 waist,
0:18:08 you are absolutely not going to find anything in ready to wear or made to measure.
0:18:09 You have to go to bespoke.
0:18:10 Most people are not that build.
0:18:12 Most people are not professional baseball players.
0:18:16 Most people are actually pretty average size, so they can usually get a good enough fit
0:18:17 in ready to wear.
0:18:20 I have some articles on, you know, where I think you can shop for a suit.
0:18:25 But the issue is still that the effort is put on you.
0:18:27 You have to figure out what are your fit issues?
0:18:28 How do you want to dress?
0:18:30 How to put together a wardrobe?
0:18:34 Someone recently emailed me with photos of a poet.
0:18:39 This person’s writing an article about this poet’s life and this poet lived somewhere
0:18:40 on the East coast.
0:18:44 Early in this poet’s life, there was photos of him as a young person, I would say like
0:18:48 in his 20s or so in the 1930s.
0:18:54 And then over time you see him in the 20s and 30s, he dressed really, really well, exceptionally
0:18:55 well.
0:18:58 Not much for the time, but looking back, like very, very well.
0:19:01 And then over time, his dress started to worsen.
0:19:06 And as I was explaining to this writer, if you can imagine this poet has an interest
0:19:11 level in clothing, we’ll say 70 out of 100.
0:19:17 In the 1920s and 30s, he just has to walk down the block to get whatever he needs.
0:19:22 And then over time, as tailoring disappears, it’s harder to find good clothiers.
0:19:29 And the number of options balloons, and there’s all these different languages, a level 70
0:19:31 is only going to get you so far.
0:19:36 Your interest level has to be 90 or 95 to get to how he dressed in the 20s and 30s, because
0:19:40 now you have to source things online, you have to do all this crazy work.
0:19:45 There’s a lot of burden now on the consumer, which is partly why it’s difficult to build
0:19:46 a wardrobe.
0:19:50 It doesn’t mean that another, a podcaster interviewed me once and he’s, and they asked,
0:19:53 you feel that most people are badly dressed.
0:19:58 And that’s a very loaded question, because I think there are many well-dressed people
0:20:01 if you understand their own dress aesthetic and language.
0:20:06 When I walk around San Francisco, I see people wearing cool hiking gear or vintage gear,
0:20:10 but they’re often like embedded in some kind of cultural community.
0:20:15 But if you’re outside of a cultural community that doesn’t have much cultural capital, because
0:20:19 that’s, in my view, how we think of aesthetics, we think of in terms of cultural capital and
0:20:20 social language.
0:20:25 If you’re outside of those communities and you’re not a punk and you’re not a cool hiker
0:20:31 or you’re not part of a rock band or whatever, then you kind of have to figure out where
0:20:34 to buy the clothes, the express an identity that you like and how it should fit and all
0:20:35 of that.
0:20:42 And yeah, it’s unfortunately a much harder uphill battle than it was 50 years ago.
0:20:47 There’s a really good, he used to teach business at University of California Berkeley, I don’t
0:20:48 know if he still does.
0:20:52 His name is Barry Schwartz and he wrote a book called The Paradox of Choice.
0:20:58 That book opens with the story of how Schwartz enters the gap and is shopping for a pair
0:21:06 of jeans and the sales associate asked him, “Do you want washed, raw, rinsed, white, dark,
0:21:11 blue, slim fit, slim straight, tapered, baggy, athletic cut?”
0:21:15 And he gave him all these options and he said he walked out that day from the gap with the
0:21:18 best pair of jeans he’s ever bought.
0:21:22 But he was left more unsatisfied than he’s ever felt because just knowing that there
0:21:27 are so many choices made him question the choice that he made that day.
0:21:32 And part of his book is that people are often better off if they’re given a much more constrained
0:21:33 number of choices.
0:21:37 So if you think of like going into an Apple store, there are very few choices and they’ve
0:21:42 constrained it to make the purchasing decision process easier, but they are, I mean, presumably
0:21:46 they think so, they’re all good choices.
0:21:50 And the problem at the moment at the market is that there are billions of choices for
0:21:56 any style of item, following any number of design languages, any number of fits, and
0:22:02 that has caused incredible anxiety in the market, which is very difficult to solve.
0:22:07 Here’s how I’m solving it is I go to your blog or people who I like or follow on Instagram
0:22:10 and I’m just like, I’m just going to do what they do.
0:22:14 And it’s sort of like when you learn how to play music, you play other people, you play
0:22:16 other people’s music for a long time.
0:22:21 And then you start feeling like, man, I love like this little riff from this rock like genre.
0:22:23 And then I like, I’m inspired a little bit by this thing.
0:22:26 And I start crafting my own because I’ve just learned the technique.
0:22:29 And I know like what’s cool and what’s not and what’s my texture with dress.
0:22:32 It’s kind of the same thing where it’s like, all right, I’m new.
0:22:37 So whatever Derek or whoever I follow on Instagram does, I’m just going to copy that and doing
0:22:42 that after a couple of years, I’m going to develop my own sense.
0:22:46 And so like the question I have for you, which is, it’s hard to know when you’re shopping
0:22:50 online, which is what I think most people in their 20 and 30s do.
0:22:52 It’s hard to know what’s good.
0:22:56 And the reason why you need to know what’s good is because if I were to follow what you
0:23:01 and a lot of people say, I would be buying so much stuff.
0:23:03 But that’s not exactly what you’re wanting me to do.
0:23:08 I think what you and what I believe is that you should buy for life.
0:23:12 You buy less things, but you buy high quality things that can last a lifetime.
0:23:16 I still struggle to figure out what those high quality things are.
0:23:22 And so my question is how should I figure out what is a high quality brand or high quality
0:23:27 product that is deserving of more money to be spent online?
0:23:28 Yeah.
0:23:32 Oh, I agree with everything you said of find people that you like and copy them on the issue
0:23:35 of how to find the quality thing.
0:23:38 So there are, it sounds like you’ve read a lot of my work.
0:23:41 So I’ve written about different ideas of how we think of quality.
0:23:43 There’s the build quality.
0:23:46 So there is such a thing as a certain kind of build quality with clothes.
0:23:50 So to give an example, leather dress shoes.
0:23:54 If you buy leather dress shoes made with a Blake stitch or Goodyear welt on the sole
0:24:01 and the uppers are made from full green leather, those shoes will age better, last longer and
0:24:02 they can be resold.
0:24:03 Like an Alden?
0:24:08 Yeah, like an Alden versus if you buy something with a glued on sole and made from corrected
0:24:13 green leather, that corrected green leather is a bad leather that’s been sanded down
0:24:18 to remove the blemishes or scars and whatnot and then coated with some chemical to make
0:24:21 it look smooth and normal again, uniform.
0:24:25 And that coating eventually flakes off, doesn’t age very well.
0:24:28 So you end up looking at your shoes and you don’t like how they look and then you go out
0:24:32 and buy a new pair, whereas full green leather will age better over time.
0:24:33 It will look more natural.
0:24:35 It gets the kind of patina that people like.
0:24:39 And then with a stitched on sole, you can always un-stitch the sole and replace it.
0:24:46 You can actually still replace glued on soles, but it’s a little bit more risky.
0:24:48 There’s only so many times you can do it.
0:24:51 And I wrote an article and put this on how to judge quality and clothing and it runs
0:24:53 through almost all of the categories.
0:24:56 I mean, you know, except, except for like Gore-Tex Park does.
0:25:02 I mean, generally speaking, sweaters, shoes, tailor jackets, you know, like woven shirts,
0:25:05 things like that, like how to think of quality.
0:25:09 But the scope of build quality is actually pretty narrow.
0:25:13 There are some things that are generally agreed upon as what is good build quality.
0:25:18 To give an example with tailor jackets, there are certain kinds of ideas of what is a better
0:25:23 or worse tailor jacket in terms of build quality, but some things are pretty subjective.
0:25:28 And if a designer is trying to bring a suit or sport coat to market, they’re working with
0:25:34 a factory and that factory has, let’s say like 300 operations.
0:25:39 There is a certain gold standard for quality, quote unquote.
0:25:45 But a designer is often not trying to sell like a five, six, $7,000 suit.
0:25:47 They’re trying to sell a $2,000 suit.
0:25:54 So they have to make design decisions on where to cut back, quote unquote.
0:26:00 And how they decide which part of those 300 operations to cut back is more, is I think
0:26:08 very subjective, but the real measure of quality should be, are you excited to put it on today?
0:26:12 And do you think you’ll be excited to put this on 10 years from now?
0:26:14 That doesn’t always mean wearing a classic aesthetic.
0:26:18 It could mean wearing something crazy because you like wearing crazy clothes.
0:26:21 And then will this thing last to some degree?
0:26:25 There is a certain kind of build quality in terms of will this thing last?
0:26:31 If you buy something and it falls apart in two years, I think most people would want
0:26:34 something that lasts a little bit longer than that, like as a physical item.
0:26:38 So I think those things, do you get excited wearing it?
0:26:42 Will it last design-wise and also kind of construction-wise?
0:26:43 And then also, does it fit and flatter you?
0:26:49 When you put it on and you look at yourself in the mirror, do you like how you look?
0:26:53 And I think those basic points, are you excited by the thing that you’re wearing and does
0:26:55 it fit and flatter you?
0:27:01 I think gets you much further than thinking of this purely as an engineering problem.
0:27:05 You can’t just read specs off a sheet like when you’re buying electronics.
0:27:08 To some degree, it’s more like food.
0:27:09 When you bite into it, does it taste good?
0:27:12 Are you excited to go out to that restaurant?
0:27:14 I think that’s a much better way to approach things.
0:27:18 It’s a more holistic way to approach things than thinking of it, just in terms of, is
0:27:20 this well-made?
0:27:24 When I was kind of up and coming in my career, I didn’t have a lot of money and I started
0:27:27 my own business and didn’t pay myself very much.
0:27:33 And so I was afraid to spend and buy things, even though I wanted stuff.
0:27:37 But even after I made a little bit of money, I was still always nervous to spend.
0:27:45 And so I see guys like you, these writers who I admire and they’ve got some great clothing.
0:27:51 And in my head, I’m wondering how many items do they actually own in their closet?
0:27:57 And up until recently, I could have gone six months without buying a clothing item.
0:28:02 Now, I think on your blog, you say, “When you first get into this shit, even if you
0:28:03 have money, buy slow.
0:28:06 Ease into it a little bit.”
0:28:09 And I’m like, pulling myself back because I’m like, “Oh, I want to get this.”
0:28:10 And I could afford it.
0:28:11 And so I’m like, “I want all this shit.”
0:28:17 How many things do you buy per month and what’s like a reasonable amount of spend, do you
0:28:20 think, for someone who can afford these things?
0:28:24 Well, I do spend a lot more than the average person, I admit that.
0:28:27 I don’t know the exact number, but to give an example, I recently bought a hoodie from
0:28:33 Bare Knuckles, I bought two double RL flannel shirts.
0:28:37 Double RL flannel shirts is what, two to 400?
0:28:41 No, I would never have bought a $400 flannel shirt.
0:28:46 I think I spent, I want to say like $175.
0:28:49 I bought a pair of Bryson cargo pants.
0:28:50 Those were kind of expensive.
0:28:51 Those were like $350.
0:28:57 But I’ve been lusting over them for like a year, so I finally just bought them.
0:29:02 Pants for this season, I don’t really imagine myself buying much for the rest of the season.
0:29:08 So I think most people are not buying two shirts, a hoodie, and a pair of pants twice
0:29:13 a year because I break up my shopping into seasons, spring, summer, fall, winter.
0:29:18 And then I do use a lot of custom tailors, and I usually have like a suit or sport coat
0:29:22 in the works through a custom tailor, and that’s been true for a while.
0:29:25 So again, most people are not doing that.
0:29:26 Those suits are getting tailored.
0:29:30 Are those bespoke or are those off the rack that you’re getting fitted to you?
0:29:31 They are bespoke.
0:29:32 That’s interesting.
0:29:37 That has always intimidated me because it seems like it’s a pain in the ass of a process.
0:29:41 And according to your, you have one post in your blog, you’re not sure if you can even
0:29:42 tell the difference all the time.
0:29:43 Yes.
0:29:48 I had this friendly argument with a good friend of mine who strongly feels that you
0:29:51 can tell, I will say I was in a DM.
0:29:56 I am in a DM with some guys who are into clothing.
0:30:01 And we were looking at a politician’s suit and we all suspect that he’s wearing bespoke
0:30:04 because of the stitching and the styling and all that.
0:30:07 And we can kind of pinpoint the region of where the tailor’s from.
0:30:12 But potentially this person is wearing like $5,000 suits is what you’re saying.
0:30:17 I would estimate that their suit probably cost around $3,000 to $4,000.
0:30:18 And then I checked their Twitter account and they followed me.
0:30:20 So I was like, maybe they do buy bespoke suits.
0:30:26 So maybe you can tell, but I’m still very skeptical of whether or not, generally speaking,
0:30:29 you can tell the difference between ready to wear and bespoke.
0:30:30 And I completely agree.
0:30:32 I think bespoke is a huge hassle.
0:30:37 There’s more misses than people let on online.
0:30:42 I think it’s very important when you go into that space to know that like not all commissions
0:30:43 turn out well.
0:30:47 It’s pretty common that commissions turn out poorly even if you’re using a good tailor,
0:30:48 but there are a lot of bad tailors.
0:30:51 One, there are some people who need bespoke.
0:30:52 We have to define it.
0:30:57 Is the terminology like off the rack and then one up from that is like made to measure,
0:31:01 which is I guess a suit supply and then is bespoke purely from scratch.
0:31:05 Well, the short answer then is ready to wear is what you go into store and can touch and
0:31:08 feel and put on yourself and put back on the rack.
0:31:13 Made to measure is something that has a block pattern, which is a pre-made pattern that
0:31:15 they adjust given your measurements.
0:31:19 You’re measured and then they adjust the pattern, make the garment straight to finish,
0:31:23 and then you come in for what they call one fitting, which means they put the garment
0:31:26 on you and they figure out, you know, what needs to be changed.
0:31:30 That fitting is basically not that much different than putting on a ready to wear garment and
0:31:32 they do adjustments.
0:31:36 The only sometimes difference is that in a made to measure garment, they have more inlay,
0:31:39 which means there’s more room for adjustment.
0:31:45 And then bespoke theoretically is that the pattern is produced from scratch.
0:31:50 And then there’s a series of fittings, typically three, basted, forward, and final fitting.
0:31:54 And then it’s sort of like, you can imagine it as someone sketching.
0:31:58 Like when you’re, you know, when I was in art class in high school, they taught us like
0:32:02 do a sketch and then you kind of like fill it in and then you kind of work it out.
0:32:03 Fitting is sort of like that.
0:32:06 The tailor sketches out what they think is going to look good and then does a fitting
0:32:09 and forgot what adjustments needs to be made.
0:32:14 And then through that iterative process, supposedly you wind up with a better garment.
0:32:19 Reality is a little bit more complex than that, but that is, that’s the general contours.
0:32:26 But your recommendation is for most people, is it ready to wear and that you get tailored?
0:32:28 Absolutely ready to wear because few reasons.
0:32:32 One is that most people are straight size, meaning they can fit into a ready to wear
0:32:36 a garment because those garments are made for the average size person.
0:32:42 And then two, the tiny differences, you’re probably not as obsessed as I am with like,
0:32:47 oh, like the quarters are not open enough and like the shoulder is, you know, you probably
0:32:49 are not like obsessed over those things.
0:32:53 Even if you are obsessed with those things, you have to like realize that like 99% of people
0:32:55 seeing you are not going to see those things.
0:33:00 And even if they do see those things, you have to be standing like a robot for someone
0:33:01 to spot those things.
0:33:05 In real life, you move around and you’re sitting and you’re interacting with the world.
0:33:11 So like all of the things that people are talking about, including me, those disappear.
0:33:14 And then the third thing is that most people don’t care about the craft element.
0:33:17 And even if they do think they care about the craft element, they probably can’t even spot
0:33:18 it.
0:33:22 So like, can you tell the difference between a machine made buttonhole and a handmade buttonhole?
0:33:24 No, of course not.
0:33:26 Very few people can, I think.
0:33:27 Yeah.
0:33:31 There are some people who need bespoke and those are people like John Fetterman will
0:33:35 never be able to fit into an off-the-rack garment or even made to measure because he’s
0:33:37 very far from the average size person.
0:33:40 He would have to go bespoke if he wanted a suit that fit.
0:33:46 But most people are not that person and the most important reason, the top tier reason
0:33:52 of why everyone should try ready where first is because you can try on the garment and
0:33:54 put it back on the rack.
0:33:58 Something happens at the end of the day, whereas with a custom garment, if the tailor offers
0:34:01 you a money back guarantee, they’re not a good tailor.
0:34:04 No good tailor will ever offer that because it takes a lot of time, effort, and money
0:34:06 to produce a good suit.
0:34:13 And then if it’s final sale, that means that if you put it on, it might not fit well.
0:34:15 There’s no guarantee that’s going to fit well.
0:34:19 But even if it does fit well, you might not like the silhouette.
0:34:21 You might have chosen a crappy fabric.
0:34:25 Maybe you asked for dumb details and then all of a sudden the garment’s produced and
0:34:28 you look at it and you realize, oh, this actually looks horrible.
0:34:31 There are many things that can go wrong.
0:34:38 And then at that point, you’ve just spent anywhere from like $2,000 to $8,000 possibly
0:34:41 for a garment and you can’t return it.
0:34:46 Whereas with a ready where garment, you can try on a $20,000 suits exist for ready where.
0:34:50 But if they did, you could try it on and put it back on the rack and nothing happens.
0:34:52 And that’s the number one reason.
0:34:58 Even if you are just getting into this and you suspect that you need a custom garment,
0:35:03 I still think you should try ready where because when you try ready to wear, you can start
0:35:05 to identify certain things.
0:35:10 You can start to say, oh, actually don’t like how I look in a very soft shoulder jacket.
0:35:15 I think I need more padding or I don’t actually like how I look in a three button jacket.
0:35:17 I think I want a two button jacket.
0:35:21 And once you start getting an eye for that silhouette, you can then start to find a
0:35:27 tailor because if you know that you want a very padded cut that narrows your options.
0:35:28 All right.
0:35:29 A quick break.
0:35:32 I know that if you’re listening to my first million, that means you love numbers.
0:35:37 Well, I’ve got a new podcast called money wise and the premise is simple.
0:35:38 We talked to high net worth people.
0:35:44 So people who have somewhere between 50 to $500 million and we start with simple premise,
0:35:49 which is tell me exactly how much money you have, how much money you make every month,
0:35:53 what your portfolio looks like, how much money you spend every month and every other
0:35:57 bit of information that involves your net worth and your spending.
0:36:02 And the reason we do this is because I want to demystify money.
0:36:06 So we just had this woman named Anne who has a $94 million portfolio after selling her
0:36:11 business and she spends $360,000 a month and she talks about where the money is and what
0:36:13 she spends it on and why she spends that much.
0:36:14 And if it makes her happy or not.
0:36:19 And then we dive deep on different topics like children buying versus renting, giving
0:36:20 money away.
0:36:23 We basically are having a conversation that I see a lot of rich people having behind closed
0:36:24 doors.
0:36:25 We do it publicly.
0:36:26 So check it out.
0:36:30 It’s called money wise and you can find it wherever you get your podcasts.
0:36:33 I have a tailor now and I don’t know if I like, like it’s kind of funny.
0:36:35 First of all, a lot of tailors.
0:36:36 Is it a red flag?
0:36:41 If your tailor dresses poorly or has poorly fitting clothes or is it like one of those things
0:36:44 where it’s like the cobbler’s kids is the last kids to get shoes.
0:36:45 You know what I mean?
0:36:46 Yeah.
0:36:47 It’s the cobbler’s kids is the last kid.
0:36:53 There are many tailors who also dress poorly because many tailors are better thought of
0:36:54 as technicians.
0:36:55 They’re not like stylists.
0:36:59 So they themselves are often just wearing something that’s not very interesting.
0:37:04 So I wouldn’t judge a tailor’s work by how they dress, but I would judge a tailor’s work
0:37:07 by the customers that come out.
0:37:13 So if the customers come out and they all are wearing suits that don’t fit, the chance
0:37:16 of you getting a good suit from that tailor is very low.
0:37:22 But if all the customers walk out and their suits fit perfectly and especially helps if
0:37:25 the customers walk out or have a similar build as you.
0:37:28 So if you are a very heavy guy and you see heavy guys walking out of the store and they
0:37:33 all have suits that fit beautifully, well, then yeah, the chance of you getting a good
0:37:35 suit from that tailor is very high.
0:37:39 So you’re not going to stake out a tailor shop and like just walk see who comes out
0:37:41 the door, but you can do this on Instagram.
0:37:48 You can go to Instagram, go to the tag section and see if the people that wear their clothes,
0:37:49 if their clothes fit well.
0:37:50 Yeah.
0:37:53 I like to collect old denim.
0:37:59 So I’ve been into salvage and raw denim since probably 2008.
0:38:00 It’s kind of a weird hobby.
0:38:02 Oh, so you are not new to this.
0:38:06 If you’re into denim in 2008, you are actually, you’re very seasoned.
0:38:09 And so you know this stuff very well.
0:38:12 Denim is my, I’m an American history nerd.
0:38:13 I’m very passionate.
0:38:16 So have you ever seen a TV show, American Pickers?
0:38:17 Yeah.
0:38:19 I used to work with Mike when I was in college.
0:38:22 That was my college job was working with Mike from American Pickers.
0:38:28 And so I got, and I’m obsessed with American history and there are two or three things that
0:38:33 are very American are denim and the leather jacket.
0:38:40 And so I’ve always owned shot leather jackets or I’ve always been, or Buko leather jackets.
0:38:41 Yeah.
0:38:45 And then like red tag Levi’s or big E Levi’s.
0:38:50 I was one of the first cover customers of I’m a Gina Willie and I would spend like ungodly
0:38:52 amounts on denim.
0:38:53 And I would say I have them all saved.
0:38:57 I’ve dozens of them saved because I want to, I read Heddles and I’ve like been the
0:38:59 fate of the Fade Friday.
0:39:00 Oh man.
0:39:03 You were presenting yourself as new to this hobby.
0:39:06 You are as seasoned as they come.
0:39:11 Anyone who says all of those words, Heddles and I’m a Gina Willie and, you know, shot
0:39:12 well.
0:39:13 Mad Carrie from I’m a Gina.
0:39:16 Like I used to go to the store all the time when I didn’t have any money and they would
0:39:18 kind of pity me and give me a shirt every once in a while.
0:39:22 And then like when I started making like $10 an hour or somewhere, I would like, I bought
0:39:26 my first I’m a Gina and I would get shrink to fit Levi’s back when I was 18.
0:39:27 I love that shit.
0:39:32 But as I got bigger, I got, I’m into weightlifting and so my legs got too big for a lot of these
0:39:33 like traditional stuff.
0:39:38 So I’ve, then I used to go to self edge and SF and get a flat head.
0:39:40 That was, anyway, the Japanese shit I love.
0:39:46 And so my point being, I spent all this money on denim and what I’ve, and it’s sort of like
0:39:50 you start as a beginner where you buy cheap shit and then you go in the middle, which
0:39:53 you buy really expensive high end stuff.
0:39:59 And then now I’ve sort of ended on the other side to where I’m just buying $30 wranglers
0:40:01 that fit well.
0:40:07 And so, but like with, with, with tailoring stuff, that’s what you’ve inspired me with
0:40:08 is tailoring stuff.
0:40:13 I’m kind of new to where I’m buying the cheap shit, thrifted stuff that, that I could tailor.
0:40:15 That’s actually pretty dope.
0:40:17 But then I’m like going to like suit supply, which is like the thousand dollar shit.
0:40:20 And I’m like, it kind of sucks.
0:40:25 I should either like go to like keep the cheap dude, cheap thrifted stuff that you get tailored
0:40:26 or go like pretty high end.
0:40:32 That journey, what you’re talking about, imagine if you started that denim journey and you’re
0:40:35 buying like 21 ounce iron hearts.
0:40:36 Yeah.
0:40:39 You would probably not even get into it because you would be like, this is insane.
0:40:40 No, it’s the pain in the butt.
0:40:41 Yeah.
0:40:42 Yeah.
0:40:47 The only way that you end up buying 21 ounce iron heart denim is if you start with 14
0:40:49 ounce iron, you like how they feel.
0:40:53 And then someone says, oh, why don’t you try 16 ounce and then you, you like, you really
0:40:54 like how I feel.
0:40:56 And then you move up and all of a sudden you’re at 21 ounce and then you like, I actually
0:41:02 do like this even though it’s no sane person would ever like this, but it’s just because
0:41:04 I’m in this hobby.
0:41:08 So that’s to me the same with rated wear with tailoring is that you start, you have to figure
0:41:10 out what you like.
0:41:11 There’s a really good book that I like.
0:41:16 It’s called Perfumes, the guide by Luca Turin and Tanya Sanchez.
0:41:17 A book on perfumes.
0:41:18 Yeah.
0:41:21 But it’s just, it’s just a, it’s just a list of reviews.
0:41:25 So it’s only helpful if you, if you’re into perfumes and you want to look up a review
0:41:27 of what someone thinks of a perfume.
0:41:33 But in the introductory chapters, Tanya Sanchez writes, I’ve talked to hundreds of people
0:41:38 who are into perfumes and they all seem to follow a similar journey.
0:41:42 In the beginning, there’s this exploration stage where you’re like finding perfumes and
0:41:46 like your mother’s wardrobe or your father’s dresser or whatever.
0:41:48 And then you explore different notes.
0:41:52 And then there’s the stage where you think you’ve found your taste and you have very
0:41:56 rigid rules about everything, your very strong opinions.
0:42:01 And then the third final step is what she feels is nirvana where you know the rules,
0:42:05 but you’re not like strict about them and you just like what you like.
0:42:10 So I think that’s actually pretty true for a lot of things, whether you’re into motorcycles
0:42:15 or whether you’re into, you know, you’re a foodie or you’re into fountain pens is that
0:42:21 people start with an exploration stage, they figure out the terrain, you know, the hills
0:42:23 are over there and the lakes are over there.
0:42:27 And then they get very adamant about rules, like everything has to be this way.
0:42:31 And then there’s a point where they just know what they like and they’re not as adamant
0:42:32 about the rules.
0:42:36 And sometimes the things that they like are not even the expensive coveted things that
0:42:40 everyone talks about, it’s just something they like.
0:42:41 And that’s it.
0:42:43 That’s the emotional, that’s the nirvana that you reach.
0:42:46 So the thing that you like might just be ranklers.
0:42:51 It’s just a pain in the ass that you have to spend as much money, that much money and
0:42:54 in a decade to go through this.
0:42:57 And that’s why I mean, that’s why I like reading your blog and reading people like you is like,
0:43:02 I’m like, how can I just like speed run some of these learnings and just not make the mistakes
0:43:03 that I’ve made before?
0:43:09 Like, for example, a big thing in clothing that that a lot of people are bringing back
0:43:11 is high rise trousers.
0:43:16 And like there was this period where we went through like slim clothing.
0:43:20 And first of all, it’s the fucking worst because it looks stupid looking back on it.
0:43:26 And it’s like incredibly uncomfortable and like half the dude, half men can’t like they
0:43:28 have big asses and big thighs.
0:43:29 Like we can’t wear that stuff.
0:43:32 Like you can only wear that stuff if you’re a smaller person.
0:43:37 But it’s like, I just wish I would have like stuck to more timeless things and thought what
0:43:43 will what was cool 50 years ago and will likely be cool in 50 years from now or what I think
0:43:44 will be cool.
0:43:48 And I just wish I wouldn’t have gone through that that that slim phase because now I have
0:43:53 so much slim stuff and I’ve spent tens of thousands of dollars probably on it.
0:43:54 Yeah.
0:44:00 I mean, I will say that that high rise, fuller leg look, I often talk about online in the
0:44:04 context of tailored clothing, if you’re if you want to dress like Mick Jagger and rock
0:44:08 and roll kind of like, you know, tight leather jackets and tight rock t-shirts, then you
0:44:10 need tight pants.
0:44:14 It only works if you’re a small, if you’re a smaller person, by the way, that I don’t
0:44:16 think you have to be a very slim dude.
0:44:22 If you’re above 510 and over like 180, it’s hard to pull that off because you just look
0:44:23 like you look stupid.
0:44:26 And I’ve tried to do that and I look so dumb.
0:44:30 I do think it helps to be a certain build for that look.
0:44:32 And then the whole look has to come together.
0:44:34 You have to again, think of it in terms of like a social language thing.
0:44:38 But if you’re wearing a tailored jacket, like a suit jacket or sport coat, I do think there
0:44:42 are certain proportions for the trousers that work better for the jacket and especially
0:44:46 is works better across a wider range of men.
0:44:51 There are some men who can wear very, very skin tight suits, but they are often very
0:44:55 thin and they usually have very broad shoulders compared to the waist.
0:44:56 They’re basically models.
0:44:58 Like if you look at runway models, they’re wearing the suits.
0:45:01 They do look good, but most people are not built like that.
0:45:04 And a jacket can only be as tight as your body allows.
0:45:10 So at some point you have to figure out how to create a trouser silhouette that works with
0:45:17 the jacket that you’re wearing and the jacket is constrained by your own body’s proportions.
0:45:18 I appreciate you coming on this podcast.
0:45:21 You’re the man and thank you for everything.
0:45:22 Thank you.
0:45:23 Thanks for having me on.
0:45:24 This was such a pleasure to be on.
0:45:25 So thank you for the opportunity.
0:45:26 Thank you.
0:45:27 And that’s the pod.
0:45:28 Thank you.
0:45:29 Thank you.
0:45:30 Bye.
0:45:31 Bye.
0:45:32 Bye.
0:45:36 Bye.
0:45:37 ♪ Body ♪
0:00:05 is for you.
0:00:06 And it’s going to be a little strange.
0:00:09 If you saw this headline, if you saw this title, you’re going to think, why on earth
0:00:11 is this happening on a business podcast?
0:00:13 Today’s episode is with Die Workwear.
0:00:18 Die Workwear is the username of a person who’s gone incredibly viral on Twitter.
0:00:21 He has over a million followers, and he talks about men’s fashion.
0:00:26 I saw this guy pop up last year, and it kind of changed my life because he taught me about
0:00:31 dress and how dressing a certain way, it gives a huge amount of confidence.
0:00:36 And the problem is that you don’t try to dress nice because you don’t really know the rules.
0:00:40 And so I thought it’d be fun to talk to Derrick about his rise, so how he got huge and built
0:00:45 the business, but also some practical tips on how to dress better and what that means
0:00:47 for your life and what that means for your confidence.
0:00:50 So give this episode a listen, and I’ll talk to you in a little bit.
0:01:02 I think the reason why you’re blowing up right now, I’ll give you my opinion, and maybe
0:01:04 you could give me your opinion.
0:01:09 But I care how I look, and I’ve always cared about that, but I never really knew the rules.
0:01:13 And basically, when you don’t know the rules of something, you feel not confident and you
0:01:16 kind of just revert back to like, well, I’m just going to do the lazy thing of like wearing
0:01:20 athleisure or like kind of boring clothes.
0:01:25 But you have this line that you repeat constantly, which is clothing is a social language.
0:01:29 And you kind of have taught people how to speak it, which kind of gives confidence.
0:01:34 And it makes your clothing feel like armor, but also you’re dressing like the person you
0:01:35 want to be.
0:01:38 And you’re speaking the language of the people who you want to speak with and kind of what
0:01:40 you want to behave like.
0:01:43 And I think this is why millions of men have liked you because you’re giving them confidence
0:01:45 and teaching them the language.
0:01:48 I do think of clothing as social language.
0:01:53 And I’ve always thought of it in that sense because, you know, if you grew up anytime
0:01:58 before the internet, you know, you may have been part of some social group around a hobby
0:02:03 or an interest like you were a skater or you’re into punk music or whatever.
0:02:07 And everyone I knew dressed a certain way to communicate an identity like they were
0:02:09 a jock or they were a nerd or whatever.
0:02:13 And there was always rules around that look, even if no one wrote a book and spelled it
0:02:14 out for you.
0:02:17 Everyone kind of knew that this was the look.
0:02:20 And everyone kind of conformed to the look of their social group and identity, and they
0:02:23 kind of broadcasted a message.
0:02:29 And I think over time, I’ve just kind of taken that idea and talked about how it’s also
0:02:35 used in classic tailoring or, you know, tech wear or whatever is the aesthetic genre.
0:02:37 People are using dress to communicate something.
0:02:43 And even people who dress in ways that is subconscious that they think they don’t care
0:02:48 about clothes, they still kind of dress according to their socio-economic class.
0:02:50 I bring up this example often.
0:02:55 There was a moment in the tech industry in the early 2000s where the hoodies and jeans
0:02:59 uniform was a way to signal, I don’t care about clothes.
0:03:04 I’m like the whiz kid, you know, kind of hacker that’s reshaping the economy.
0:03:07 All I care is about meritocracy and skills.
0:03:10 But it just so happens that over time within that industry, everyone started to also dress
0:03:11 the same.
0:03:16 So to some degree, people are at least conscious of what is the look within their group.
0:03:21 And they were careful to not deviate too far from it because they want to signal that
0:03:22 they belong.
0:03:26 There’s a there’s an article that I often mention on Twitter and sometimes in interviews.
0:03:28 The author’s name is Carlos, but I can’t remember his last name.
0:03:33 But he wrote an article called inside the meritocracy mirror, like looking into the
0:03:34 mirror and then talk.
0:03:38 And in his article was about how even in the tech industry where people say they don’t
0:03:42 care about clothes, everyone mirrors each other.
0:03:47 And clothes do play a part because if you showed up to a job interview for the tech
0:03:51 industry and you wore a three piece suit, people assume that you don’t fit in and they
0:03:53 will read something into your clothes.
0:03:55 So to some degree, clothes do matter.
0:03:59 Hey, let’s take a quick break.
0:04:00 I want to talk to the marketers out there.
0:04:04 We all know that marketers have never been so spread that you got to create content.
0:04:05 You got to launch campaigns.
0:04:06 You got to get leads.
0:04:07 You got to score the leads.
0:04:08 Nurture the leads.
0:04:10 You got to have a second to breathe, let alone do your best marketing.
0:04:14 That is where HubSpot and Breeze, its new built in AI, come in.
0:04:18 So with this, you can do things like instantly remix your content.
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0:04:25 And they have an AI curated analytics suite, so you can get reports and KPIs.
0:04:29 Stop spreading yourself then and start making major moves with HubSpot.
0:04:34 Visit hubspot.com/marketers to learn more.
0:04:39 This is the first time we’ve ever done an anonymous podcast and I want to ask you about
0:04:40 your rise.
0:04:43 So if there’s ever anything that you just don’t want to answer, just let me know.
0:04:48 But is this your full-time gig now, which is kind of being a writer or whatever it is
0:04:50 you describe yourself as?
0:04:54 Yeah, I make my living off writing about menswear.
0:04:59 There’s this concept that I think I learned from you or a rabbit hole you sent me down.
0:05:04 Is it called a sprezzatura where it’s like you’re being careless, but that’s kind of
0:05:05 the cool part, right?
0:05:07 It’s like not trying too hard, but you look amazing.
0:05:09 Did I explain that accurately?
0:05:15 Yes, it was originally introduced by an Italian writer during the 16th, 17th century.
0:05:23 And the writer who originally used this term was describing how to serve the king.
0:05:28 And they were saying that you should do things in a way that conceals your effort.
0:05:34 An easy way to understand this is like if Sam asked me to do a favor, can you pick up
0:05:38 my car from this location and drive it to this place?
0:05:41 I will do the favor, but insist that it’s no big deal.
0:05:42 It’s not a problem.
0:05:43 Don’t worry about it.
0:05:50 Even if it is actually kind of inconvenient, and it’s a way to essentially, I guess serve
0:05:55 you, is to make the person feel good about what they’ve asked of you.
0:06:03 The sprezzatura in a men’s style sense is basically to dress in a way that conceals the effort
0:06:05 that you’ve put in.
0:06:08 But the concept goes way back before this writer.
0:06:14 It goes back to even Brummel, who is largely understood to have shaped much of moderns
0:06:15 men’s style.
0:06:21 And Brummel used to spend hours tying his cravat, his white cravat, which is kind of
0:06:22 like a necrochiff.
0:06:28 This is a famous story, probably made up, but the story is that one of his valets was
0:06:33 seen exiting the room once with a huge pile of cravats, and someone asked him, “What are
0:06:34 those for?”
0:06:37 And he said, “These are our failures.”
0:06:41 And the idea was that Brummel actually spent hours and hours and hours in the morning putting
0:06:42 together his look.
0:06:46 And then he’d walk out and then pretend that he just happened to have fell into these clothes.
0:06:48 Like it was no big deal.
0:06:50 It was a complete natural thing.
0:06:52 He woke up like this.
0:06:56 And that is part of the idea that style is kind of a natural extension of you, and it’s
0:06:58 not an artifice.
0:07:02 And that’s sort of, you’re doing Spresitaro with your Twitter handle and with your writing
0:07:03 and with your reach.
0:07:07 You’re like, “Oh, I just kind of just wrote what came interesting.
0:07:14 And I don’t know how big it is, but in reality, you’re just behind the scenes just scheming.
0:07:19 You’re just, you’re like, “Oh, I just wrote this really funny burn to this guy who replied.”
0:07:23 And it just happened to get 2 million views because that’s one of the things that you
0:07:29 do, which is pretty funny, is you reply to a couple of people, but you murder them.
0:07:30 It’s called murdered with words.
0:07:34 You just kind of annihilate them.
0:07:37 And that’s kind of your style, which I find hilarious.
0:07:41 But one person you’ve turned me onto is Ralph Lauren.
0:07:45 And Ralph Lauren has an interesting story, but I’m like getting obsessed with some of
0:07:49 his quotes because he was raised a very normal background.
0:07:52 But he said that he got obsessed with movies at a young age.
0:07:57 He was like, I’m not sure if I can be an actor, but I can design my life via clothing.
0:08:00 If I put on a farmer’s outfit, I’ll feel like a farmer.
0:08:03 If I put on a soldier style office, I’m going to feel like a soldier.
0:08:04 I’ll feel tough and brave.
0:08:05 And he has this great quote.
0:08:07 He says, “I don’t design clothes.
0:08:12 I design dreams.” And then he dresses as if whatever he wants to become.
0:08:14 He was a Jewish kid from the Bronx.
0:08:17 He was like, I want to feel like this old money sophistication.
0:08:19 So we started dressing like that and he became it.
0:08:23 And I think that’s what is interesting about what you’ve opened up to a lot of people is
0:08:26 this idea of acting as if and then you become.
0:08:27 Yeah.
0:08:30 If you go through a Ralph Lauren flagship, it’s not true for the normal stores.
0:08:33 The normal stores are just normal stores, but if you visit a Ralph Lauren flagship,
0:08:37 it’s like walking through like Epcot Center, like the amusement parks and there’s like
0:08:40 the pirate ship world and there’s a rocket ship world and all that.
0:08:43 You go through a Ralph Lauren flagship, there’s like the ranch world.
0:08:45 There’s the old money world.
0:08:48 There’s, you know, there’s all these different worlds that he creates around costumes.
0:08:54 And it’s because he knows how to imbue you with both that fantasy and to kind of use
0:09:00 that language and design to reference different social ideas and identities.
0:09:03 I want to ask you practical tips on like dress and things like that.
0:09:07 But I actually want to ask you practical tips first on learning.
0:09:09 I’ve noticed that you’re pretty insane.
0:09:14 Like I read a blog where it starts off like saying in the 1959 book, try for elegance,
0:09:16 which enters around men’s clothing.
0:09:19 And then you like quote the book and you tell a story about the book and that leads into
0:09:20 the rest of your writing.
0:09:22 I went and tried to find that book.
0:09:25 That was a book that’s out of print.
0:09:29 That’s like $300 or something like that and it has like no reviews on Amazon.
0:09:33 And then you’ll do like the history of tweed.
0:09:36 And I’m like, how the hell do you know this shit?
0:09:40 And so what I want to know is how are you learning all of these things and storing the
0:09:41 knowledge?
0:09:46 That’s what fascinates me about you is like your mastery of a topic.
0:09:50 That comes with a lot of buying stuff that ends up being crappy.
0:09:54 So I’ve bought a lot of books on clothing.
0:09:58 If they’re, you know, especially old books and if it was published in some, you know,
0:10:01 some time, you know, this obscure book I’d buy and then read it and a lot of that stuff
0:10:03 ends up being crappy.
0:10:05 But sometimes there’s like a nugget over time.
0:10:08 I think you get a better sense of like, which books to buy obviously you’re not just constantly
0:10:12 doing the scattershot, but I do end up buying a lot of books and then reading them.
0:10:15 And then sometimes there’s like a nugget here and there.
0:10:16 It does help.
0:10:22 I would say that fashion as a topic for a while was not treated seriously.
0:10:27 And then to the degree it is treated seriously, it’s often focused on women’s clothing.
0:10:34 And then to the degree that men’s clothing is taken seriously, there are many brilliant
0:10:39 academic writers who focus on men’s clothing, but they tend to be extremely academic.
0:10:47 So I am in a space where I’m just enthusiast and I try to write something that ties clothing
0:10:53 into other parts of culture, which I hope makes it more interesting to everyday people.
0:10:56 And I try to do something that’s a little bit smarter than just like basic trend reporting
0:11:00 or fashion writing, but it’s a little bit more accessible than academic writing.
0:11:03 And then I also tread this water where not a lot of people are treading.
0:11:05 And I think that kind of helps.
0:11:09 I think it helps to be in this very specific space.
0:11:16 Today you had a thing about like the quarter zip and like that caused so much, so much outrage.
0:11:19 And I think I said you were coming on, I got so many people that are pissed off that you
0:11:25 were coming because they were like, dude, he’s so unrelatable to the middle America guy.
0:11:28 And I think though that oddly those people are folks that are being turned on to you
0:11:29 right now.
0:11:33 What are the common issues that they come to you with?
0:11:37 And what’s the general advice to the three most common things for like, if you do this,
0:11:42 this and this, you’re going to be 60% of the way there or significantly better.
0:11:45 You can’t answer any of those things without first thinking of closed social language and
0:11:48 the thinking of what you want to communicate.
0:11:52 So if you think of closed social language, you are to me like 90% of the way there because
0:11:55 then you can think of like how something should fit and the colors and the styles and all
0:11:57 that to combine.
0:12:01 I admit that as my account has grown, I’ve leaned a little bit more towards tailoring.
0:12:05 Before my account started grow, I talked about a much wider range of styles, often like Japanese
0:12:06 workwear or something.
0:12:11 And I’ve leaned a little bit more into tailoring because that’s an aesthetic language that
0:12:12 I think more people understand.
0:12:14 Is that limited to suits?
0:12:19 Good sport coats, anything that would be considered like maybe smart casuals.
0:12:22 I think there are certain kind of aesthetics that like everyone recognizes, oh, that’s
0:12:23 good.
0:12:25 Again, bringing it back to language.
0:12:30 If you think of like dialects, received pronunciation, everyone recognizes that as like the quote
0:12:34 unquote correct pronunciation.
0:12:36 And they recognize that as the good English.
0:12:39 But you know, throughout the UK, there are many dialects.
0:12:44 And even though everyone recognizes received pronunciation as the dialect.
0:12:49 If you speak received pronunciation in certain parts of England, you might come off as kind
0:12:54 of crazy because everyone there speaks in a different dialect.
0:12:59 But if you take that dialect and put it across the nation, a lot of people are going to be
0:13:03 very opinionated on whether or not that is the correct way of speaking because that’s
0:13:04 very regional.
0:13:10 So there are certain modes of communication that are hegemonic and suit sport coats, but
0:13:15 a certain kind of like dressy kind of look is what I would consider hegemonic and visual
0:13:17 aesthetics.
0:13:24 Even though wearing a chore coat or wearing a punk rock biker jacket or other aesthetics
0:13:29 can be legitimate in their own way, it’s just that if you present that to other people,
0:13:34 it’s more controversial and fewer people are going to recognize it as quote unquote good
0:13:35 because it’s so regional.
0:13:40 The problem with I will admit when you talk about like the Midwestern guy, I get this a
0:13:46 lot is that somebody from outside of San Francisco or New York City or Los Angeles to say, “I
0:13:48 really like what you put out there.
0:13:50 How can I dress like this?”
0:13:57 And that is sometimes a question I can’t answer because if you want to wear sport coats and
0:14:03 you live outside of a handful of cities, and especially if you’re fall outside of straight
0:14:08 sizing, let’s say you’re a size 46 chest, I just got an email the other day, someone has
0:14:13 a 48 chest, but a 32 waist, so they’re a professional baseball player.
0:14:19 If you’re that build and you are outside of the major cities, I don’t really have an answer
0:14:23 for you because tailoring has died over the last few decades.
0:14:24 There aren’t many good tailors.
0:14:28 So what you’re going to find is a lot of ready to wear tailoring, which is not going to fit
0:14:30 an unusual build.
0:14:34 And then you also have to be the kind of guy that’s willing to wear a sport coat, even
0:14:37 though other people aren’t wearing a sport coat.
0:14:42 You have to put up with the fact that you are overdressed and you’re doing it for yourself
0:14:44 and it’s pleasing to you.
0:14:49 So sometimes if you’re in a smaller city, there may not be a lot of options and there
0:14:53 may be, I think, harsher judgments.
0:14:58 Whereas I think in a big city, you have a certain kind of anonymity where you can dress very
0:15:01 different from others and nobody cares.
0:15:06 Like nobody cares if you arrive to the office in a sport coat and everyone’s dressed down.
0:15:08 I’d still think you can in a small city.
0:15:11 I have a friend who works for a religious organization.
0:15:13 He lives just outside of Nashville.
0:15:15 Yeah, men musing.
0:15:16 Gentlemen musing.
0:15:18 Yeah, men’s wear musings.
0:15:19 Mitchell.
0:15:20 Yeah.
0:15:26 He works for a religious organization and he wears a sport coat with jeans to the office.
0:15:30 He told me that nobody in his office wears tailor clothing except for the really old
0:15:31 guys.
0:15:34 But he does it so often now that that’s just like him.
0:15:39 And one, he’s obviously not going to get fired for it, but two, it’s not like anyone comments
0:15:40 on it anymore.
0:15:41 It’s just him.
0:15:45 And I think it does take that kind of personality and it takes a willingness to really hunt
0:15:51 for those ready to wear pieces to figure out how things fit because historically, men dressed
0:15:56 well in tailored clothing, not because they knew all of this stuff, it’s because they
0:16:00 went to a local clotheir and that clotheir like outfitted them.
0:16:04 They, you know, you go to your clotheir and you’d say, I have to go to a summer wedding
0:16:08 or I work in this office, like just figure out how am I supposed to dress and that clotheir
0:16:10 told you, you’re going to summer wedding.
0:16:12 This is the thing that you’re supposed to wear and they’d figure out how it’s supposed
0:16:16 to fit and they do all the tailoring and all that and you walk out and you look amazing.
0:16:21 Those clothes have disappeared and customer loyalty is no longer there as well.
0:16:27 So whereas a man used to go to his tailor and would introduce his son to his tailor.
0:16:33 Now men shot from different places, not only different aesthetics, but they might buy their
0:16:37 jeans from a jean company shirts from a shirt company socks from a sock company.
0:16:42 Sometimes they’re also buying the stuff online where there’s no sales associate to guide them
0:16:47 and then they have to figure out how to put together not only a good outfit, but also
0:16:52 a good wardrobe and how to use that wardrobe to move throughout different social spaces.
0:16:59 All right, my friends, I have a new podcast for you guys to check out.
0:17:05 It’s called content is profit and it’s hosted by Luis and Fonzie cameo and it’s brought
0:17:08 to you by the HubSpot podcast network.
0:17:12 After years of building content teams and frameworks for companies like Red Bull and
0:17:17 Orange Theory Fitness, Luis and Fonzie are on a mission to bridge the gap between content
0:17:18 and revenue.
0:17:21 In each episode, you’re going to hear from top entrepreneurs and creators and you’re
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0:17:46 All right, you’re telling me this and I’m like, all right, I’m bought into all that,
0:17:47 but I feel hopeless.
0:17:49 So I live right outside New York City.
0:17:50 So it’s okay for me.
0:17:54 I can go to New York City, but I still feel hopeless where I’m like, this sounds super
0:17:55 intimidating finding a tailor.
0:17:56 Yeah.
0:17:59 There are solutions depending, everyone has to figure out their own specific situation.
0:18:04 If you’re the guy that emailed me recently, he’s a baseball player, 48 chest, 32 waist,
0:18:08 you are absolutely not going to find anything in ready to wear or made to measure.
0:18:09 You have to go to bespoke.
0:18:10 Most people are not that build.
0:18:12 Most people are not professional baseball players.
0:18:16 Most people are actually pretty average size, so they can usually get a good enough fit
0:18:17 in ready to wear.
0:18:20 I have some articles on, you know, where I think you can shop for a suit.
0:18:25 But the issue is still that the effort is put on you.
0:18:27 You have to figure out what are your fit issues?
0:18:28 How do you want to dress?
0:18:30 How to put together a wardrobe?
0:18:34 Someone recently emailed me with photos of a poet.
0:18:39 This person’s writing an article about this poet’s life and this poet lived somewhere
0:18:40 on the East coast.
0:18:44 Early in this poet’s life, there was photos of him as a young person, I would say like
0:18:48 in his 20s or so in the 1930s.
0:18:54 And then over time you see him in the 20s and 30s, he dressed really, really well, exceptionally
0:18:55 well.
0:18:58 Not much for the time, but looking back, like very, very well.
0:19:01 And then over time, his dress started to worsen.
0:19:06 And as I was explaining to this writer, if you can imagine this poet has an interest
0:19:11 level in clothing, we’ll say 70 out of 100.
0:19:17 In the 1920s and 30s, he just has to walk down the block to get whatever he needs.
0:19:22 And then over time, as tailoring disappears, it’s harder to find good clothiers.
0:19:29 And the number of options balloons, and there’s all these different languages, a level 70
0:19:31 is only going to get you so far.
0:19:36 Your interest level has to be 90 or 95 to get to how he dressed in the 20s and 30s, because
0:19:40 now you have to source things online, you have to do all this crazy work.
0:19:45 There’s a lot of burden now on the consumer, which is partly why it’s difficult to build
0:19:46 a wardrobe.
0:19:50 It doesn’t mean that another, a podcaster interviewed me once and he’s, and they asked,
0:19:53 you feel that most people are badly dressed.
0:19:58 And that’s a very loaded question, because I think there are many well-dressed people
0:20:01 if you understand their own dress aesthetic and language.
0:20:06 When I walk around San Francisco, I see people wearing cool hiking gear or vintage gear,
0:20:10 but they’re often like embedded in some kind of cultural community.
0:20:15 But if you’re outside of a cultural community that doesn’t have much cultural capital, because
0:20:19 that’s, in my view, how we think of aesthetics, we think of in terms of cultural capital and
0:20:20 social language.
0:20:25 If you’re outside of those communities and you’re not a punk and you’re not a cool hiker
0:20:31 or you’re not part of a rock band or whatever, then you kind of have to figure out where
0:20:34 to buy the clothes, the express an identity that you like and how it should fit and all
0:20:35 of that.
0:20:42 And yeah, it’s unfortunately a much harder uphill battle than it was 50 years ago.
0:20:47 There’s a really good, he used to teach business at University of California Berkeley, I don’t
0:20:48 know if he still does.
0:20:52 His name is Barry Schwartz and he wrote a book called The Paradox of Choice.
0:20:58 That book opens with the story of how Schwartz enters the gap and is shopping for a pair
0:21:06 of jeans and the sales associate asked him, “Do you want washed, raw, rinsed, white, dark,
0:21:11 blue, slim fit, slim straight, tapered, baggy, athletic cut?”
0:21:15 And he gave him all these options and he said he walked out that day from the gap with the
0:21:18 best pair of jeans he’s ever bought.
0:21:22 But he was left more unsatisfied than he’s ever felt because just knowing that there
0:21:27 are so many choices made him question the choice that he made that day.
0:21:32 And part of his book is that people are often better off if they’re given a much more constrained
0:21:33 number of choices.
0:21:37 So if you think of like going into an Apple store, there are very few choices and they’ve
0:21:42 constrained it to make the purchasing decision process easier, but they are, I mean, presumably
0:21:46 they think so, they’re all good choices.
0:21:50 And the problem at the moment at the market is that there are billions of choices for
0:21:56 any style of item, following any number of design languages, any number of fits, and
0:22:02 that has caused incredible anxiety in the market, which is very difficult to solve.
0:22:07 Here’s how I’m solving it is I go to your blog or people who I like or follow on Instagram
0:22:10 and I’m just like, I’m just going to do what they do.
0:22:14 And it’s sort of like when you learn how to play music, you play other people, you play
0:22:16 other people’s music for a long time.
0:22:21 And then you start feeling like, man, I love like this little riff from this rock like genre.
0:22:23 And then I like, I’m inspired a little bit by this thing.
0:22:26 And I start crafting my own because I’ve just learned the technique.
0:22:29 And I know like what’s cool and what’s not and what’s my texture with dress.
0:22:32 It’s kind of the same thing where it’s like, all right, I’m new.
0:22:37 So whatever Derek or whoever I follow on Instagram does, I’m just going to copy that and doing
0:22:42 that after a couple of years, I’m going to develop my own sense.
0:22:46 And so like the question I have for you, which is, it’s hard to know when you’re shopping
0:22:50 online, which is what I think most people in their 20 and 30s do.
0:22:52 It’s hard to know what’s good.
0:22:56 And the reason why you need to know what’s good is because if I were to follow what you
0:23:01 and a lot of people say, I would be buying so much stuff.
0:23:03 But that’s not exactly what you’re wanting me to do.
0:23:08 I think what you and what I believe is that you should buy for life.
0:23:12 You buy less things, but you buy high quality things that can last a lifetime.
0:23:16 I still struggle to figure out what those high quality things are.
0:23:22 And so my question is how should I figure out what is a high quality brand or high quality
0:23:27 product that is deserving of more money to be spent online?
0:23:28 Yeah.
0:23:32 Oh, I agree with everything you said of find people that you like and copy them on the issue
0:23:35 of how to find the quality thing.
0:23:38 So there are, it sounds like you’ve read a lot of my work.
0:23:41 So I’ve written about different ideas of how we think of quality.
0:23:43 There’s the build quality.
0:23:46 So there is such a thing as a certain kind of build quality with clothes.
0:23:50 So to give an example, leather dress shoes.
0:23:54 If you buy leather dress shoes made with a Blake stitch or Goodyear welt on the sole
0:24:01 and the uppers are made from full green leather, those shoes will age better, last longer and
0:24:02 they can be resold.
0:24:03 Like an Alden?
0:24:08 Yeah, like an Alden versus if you buy something with a glued on sole and made from corrected
0:24:13 green leather, that corrected green leather is a bad leather that’s been sanded down
0:24:18 to remove the blemishes or scars and whatnot and then coated with some chemical to make
0:24:21 it look smooth and normal again, uniform.
0:24:25 And that coating eventually flakes off, doesn’t age very well.
0:24:28 So you end up looking at your shoes and you don’t like how they look and then you go out
0:24:32 and buy a new pair, whereas full green leather will age better over time.
0:24:33 It will look more natural.
0:24:35 It gets the kind of patina that people like.
0:24:39 And then with a stitched on sole, you can always un-stitch the sole and replace it.
0:24:46 You can actually still replace glued on soles, but it’s a little bit more risky.
0:24:48 There’s only so many times you can do it.
0:24:51 And I wrote an article and put this on how to judge quality and clothing and it runs
0:24:53 through almost all of the categories.
0:24:56 I mean, you know, except, except for like Gore-Tex Park does.
0:25:02 I mean, generally speaking, sweaters, shoes, tailor jackets, you know, like woven shirts,
0:25:05 things like that, like how to think of quality.
0:25:09 But the scope of build quality is actually pretty narrow.
0:25:13 There are some things that are generally agreed upon as what is good build quality.
0:25:18 To give an example with tailor jackets, there are certain kinds of ideas of what is a better
0:25:23 or worse tailor jacket in terms of build quality, but some things are pretty subjective.
0:25:28 And if a designer is trying to bring a suit or sport coat to market, they’re working with
0:25:34 a factory and that factory has, let’s say like 300 operations.
0:25:39 There is a certain gold standard for quality, quote unquote.
0:25:45 But a designer is often not trying to sell like a five, six, $7,000 suit.
0:25:47 They’re trying to sell a $2,000 suit.
0:25:54 So they have to make design decisions on where to cut back, quote unquote.
0:26:00 And how they decide which part of those 300 operations to cut back is more, is I think
0:26:08 very subjective, but the real measure of quality should be, are you excited to put it on today?
0:26:12 And do you think you’ll be excited to put this on 10 years from now?
0:26:14 That doesn’t always mean wearing a classic aesthetic.
0:26:18 It could mean wearing something crazy because you like wearing crazy clothes.
0:26:21 And then will this thing last to some degree?
0:26:25 There is a certain kind of build quality in terms of will this thing last?
0:26:31 If you buy something and it falls apart in two years, I think most people would want
0:26:34 something that lasts a little bit longer than that, like as a physical item.
0:26:38 So I think those things, do you get excited wearing it?
0:26:42 Will it last design-wise and also kind of construction-wise?
0:26:43 And then also, does it fit and flatter you?
0:26:49 When you put it on and you look at yourself in the mirror, do you like how you look?
0:26:53 And I think those basic points, are you excited by the thing that you’re wearing and does
0:26:55 it fit and flatter you?
0:27:01 I think gets you much further than thinking of this purely as an engineering problem.
0:27:05 You can’t just read specs off a sheet like when you’re buying electronics.
0:27:08 To some degree, it’s more like food.
0:27:09 When you bite into it, does it taste good?
0:27:12 Are you excited to go out to that restaurant?
0:27:14 I think that’s a much better way to approach things.
0:27:18 It’s a more holistic way to approach things than thinking of it, just in terms of, is
0:27:20 this well-made?
0:27:24 When I was kind of up and coming in my career, I didn’t have a lot of money and I started
0:27:27 my own business and didn’t pay myself very much.
0:27:33 And so I was afraid to spend and buy things, even though I wanted stuff.
0:27:37 But even after I made a little bit of money, I was still always nervous to spend.
0:27:45 And so I see guys like you, these writers who I admire and they’ve got some great clothing.
0:27:51 And in my head, I’m wondering how many items do they actually own in their closet?
0:27:57 And up until recently, I could have gone six months without buying a clothing item.
0:28:02 Now, I think on your blog, you say, “When you first get into this shit, even if you
0:28:03 have money, buy slow.
0:28:06 Ease into it a little bit.”
0:28:09 And I’m like, pulling myself back because I’m like, “Oh, I want to get this.”
0:28:10 And I could afford it.
0:28:11 And so I’m like, “I want all this shit.”
0:28:17 How many things do you buy per month and what’s like a reasonable amount of spend, do you
0:28:20 think, for someone who can afford these things?
0:28:24 Well, I do spend a lot more than the average person, I admit that.
0:28:27 I don’t know the exact number, but to give an example, I recently bought a hoodie from
0:28:33 Bare Knuckles, I bought two double RL flannel shirts.
0:28:37 Double RL flannel shirts is what, two to 400?
0:28:41 No, I would never have bought a $400 flannel shirt.
0:28:46 I think I spent, I want to say like $175.
0:28:49 I bought a pair of Bryson cargo pants.
0:28:50 Those were kind of expensive.
0:28:51 Those were like $350.
0:28:57 But I’ve been lusting over them for like a year, so I finally just bought them.
0:29:02 Pants for this season, I don’t really imagine myself buying much for the rest of the season.
0:29:08 So I think most people are not buying two shirts, a hoodie, and a pair of pants twice
0:29:13 a year because I break up my shopping into seasons, spring, summer, fall, winter.
0:29:18 And then I do use a lot of custom tailors, and I usually have like a suit or sport coat
0:29:22 in the works through a custom tailor, and that’s been true for a while.
0:29:25 So again, most people are not doing that.
0:29:26 Those suits are getting tailored.
0:29:30 Are those bespoke or are those off the rack that you’re getting fitted to you?
0:29:31 They are bespoke.
0:29:32 That’s interesting.
0:29:37 That has always intimidated me because it seems like it’s a pain in the ass of a process.
0:29:41 And according to your, you have one post in your blog, you’re not sure if you can even
0:29:42 tell the difference all the time.
0:29:43 Yes.
0:29:48 I had this friendly argument with a good friend of mine who strongly feels that you
0:29:51 can tell, I will say I was in a DM.
0:29:56 I am in a DM with some guys who are into clothing.
0:30:01 And we were looking at a politician’s suit and we all suspect that he’s wearing bespoke
0:30:04 because of the stitching and the styling and all that.
0:30:07 And we can kind of pinpoint the region of where the tailor’s from.
0:30:12 But potentially this person is wearing like $5,000 suits is what you’re saying.
0:30:17 I would estimate that their suit probably cost around $3,000 to $4,000.
0:30:18 And then I checked their Twitter account and they followed me.
0:30:20 So I was like, maybe they do buy bespoke suits.
0:30:26 So maybe you can tell, but I’m still very skeptical of whether or not, generally speaking,
0:30:29 you can tell the difference between ready to wear and bespoke.
0:30:30 And I completely agree.
0:30:32 I think bespoke is a huge hassle.
0:30:37 There’s more misses than people let on online.
0:30:42 I think it’s very important when you go into that space to know that like not all commissions
0:30:43 turn out well.
0:30:47 It’s pretty common that commissions turn out poorly even if you’re using a good tailor,
0:30:48 but there are a lot of bad tailors.
0:30:51 One, there are some people who need bespoke.
0:30:52 We have to define it.
0:30:57 Is the terminology like off the rack and then one up from that is like made to measure,
0:31:01 which is I guess a suit supply and then is bespoke purely from scratch.
0:31:05 Well, the short answer then is ready to wear is what you go into store and can touch and
0:31:08 feel and put on yourself and put back on the rack.
0:31:13 Made to measure is something that has a block pattern, which is a pre-made pattern that
0:31:15 they adjust given your measurements.
0:31:19 You’re measured and then they adjust the pattern, make the garment straight to finish,
0:31:23 and then you come in for what they call one fitting, which means they put the garment
0:31:26 on you and they figure out, you know, what needs to be changed.
0:31:30 That fitting is basically not that much different than putting on a ready to wear garment and
0:31:32 they do adjustments.
0:31:36 The only sometimes difference is that in a made to measure garment, they have more inlay,
0:31:39 which means there’s more room for adjustment.
0:31:45 And then bespoke theoretically is that the pattern is produced from scratch.
0:31:50 And then there’s a series of fittings, typically three, basted, forward, and final fitting.
0:31:54 And then it’s sort of like, you can imagine it as someone sketching.
0:31:58 Like when you’re, you know, when I was in art class in high school, they taught us like
0:32:02 do a sketch and then you kind of like fill it in and then you kind of work it out.
0:32:03 Fitting is sort of like that.
0:32:06 The tailor sketches out what they think is going to look good and then does a fitting
0:32:09 and forgot what adjustments needs to be made.
0:32:14 And then through that iterative process, supposedly you wind up with a better garment.
0:32:19 Reality is a little bit more complex than that, but that is, that’s the general contours.
0:32:26 But your recommendation is for most people, is it ready to wear and that you get tailored?
0:32:28 Absolutely ready to wear because few reasons.
0:32:32 One is that most people are straight size, meaning they can fit into a ready to wear
0:32:36 a garment because those garments are made for the average size person.
0:32:42 And then two, the tiny differences, you’re probably not as obsessed as I am with like,
0:32:47 oh, like the quarters are not open enough and like the shoulder is, you know, you probably
0:32:49 are not like obsessed over those things.
0:32:53 Even if you are obsessed with those things, you have to like realize that like 99% of people
0:32:55 seeing you are not going to see those things.
0:33:00 And even if they do see those things, you have to be standing like a robot for someone
0:33:01 to spot those things.
0:33:05 In real life, you move around and you’re sitting and you’re interacting with the world.
0:33:11 So like all of the things that people are talking about, including me, those disappear.
0:33:14 And then the third thing is that most people don’t care about the craft element.
0:33:17 And even if they do think they care about the craft element, they probably can’t even spot
0:33:18 it.
0:33:22 So like, can you tell the difference between a machine made buttonhole and a handmade buttonhole?
0:33:24 No, of course not.
0:33:26 Very few people can, I think.
0:33:27 Yeah.
0:33:31 There are some people who need bespoke and those are people like John Fetterman will
0:33:35 never be able to fit into an off-the-rack garment or even made to measure because he’s
0:33:37 very far from the average size person.
0:33:40 He would have to go bespoke if he wanted a suit that fit.
0:33:46 But most people are not that person and the most important reason, the top tier reason
0:33:52 of why everyone should try ready where first is because you can try on the garment and
0:33:54 put it back on the rack.
0:33:58 Something happens at the end of the day, whereas with a custom garment, if the tailor offers
0:34:01 you a money back guarantee, they’re not a good tailor.
0:34:04 No good tailor will ever offer that because it takes a lot of time, effort, and money
0:34:06 to produce a good suit.
0:34:13 And then if it’s final sale, that means that if you put it on, it might not fit well.
0:34:15 There’s no guarantee that’s going to fit well.
0:34:19 But even if it does fit well, you might not like the silhouette.
0:34:21 You might have chosen a crappy fabric.
0:34:25 Maybe you asked for dumb details and then all of a sudden the garment’s produced and
0:34:28 you look at it and you realize, oh, this actually looks horrible.
0:34:31 There are many things that can go wrong.
0:34:38 And then at that point, you’ve just spent anywhere from like $2,000 to $8,000 possibly
0:34:41 for a garment and you can’t return it.
0:34:46 Whereas with a ready where garment, you can try on a $20,000 suits exist for ready where.
0:34:50 But if they did, you could try it on and put it back on the rack and nothing happens.
0:34:52 And that’s the number one reason.
0:34:58 Even if you are just getting into this and you suspect that you need a custom garment,
0:35:03 I still think you should try ready where because when you try ready to wear, you can start
0:35:05 to identify certain things.
0:35:10 You can start to say, oh, actually don’t like how I look in a very soft shoulder jacket.
0:35:15 I think I need more padding or I don’t actually like how I look in a three button jacket.
0:35:17 I think I want a two button jacket.
0:35:21 And once you start getting an eye for that silhouette, you can then start to find a
0:35:27 tailor because if you know that you want a very padded cut that narrows your options.
0:35:28 All right.
0:35:29 A quick break.
0:35:32 I know that if you’re listening to my first million, that means you love numbers.
0:35:37 Well, I’ve got a new podcast called money wise and the premise is simple.
0:35:38 We talked to high net worth people.
0:35:44 So people who have somewhere between 50 to $500 million and we start with simple premise,
0:35:49 which is tell me exactly how much money you have, how much money you make every month,
0:35:53 what your portfolio looks like, how much money you spend every month and every other
0:35:57 bit of information that involves your net worth and your spending.
0:36:02 And the reason we do this is because I want to demystify money.
0:36:06 So we just had this woman named Anne who has a $94 million portfolio after selling her
0:36:11 business and she spends $360,000 a month and she talks about where the money is and what
0:36:13 she spends it on and why she spends that much.
0:36:14 And if it makes her happy or not.
0:36:19 And then we dive deep on different topics like children buying versus renting, giving
0:36:20 money away.
0:36:23 We basically are having a conversation that I see a lot of rich people having behind closed
0:36:24 doors.
0:36:25 We do it publicly.
0:36:26 So check it out.
0:36:30 It’s called money wise and you can find it wherever you get your podcasts.
0:36:33 I have a tailor now and I don’t know if I like, like it’s kind of funny.
0:36:35 First of all, a lot of tailors.
0:36:36 Is it a red flag?
0:36:41 If your tailor dresses poorly or has poorly fitting clothes or is it like one of those things
0:36:44 where it’s like the cobbler’s kids is the last kids to get shoes.
0:36:45 You know what I mean?
0:36:46 Yeah.
0:36:47 It’s the cobbler’s kids is the last kid.
0:36:53 There are many tailors who also dress poorly because many tailors are better thought of
0:36:54 as technicians.
0:36:55 They’re not like stylists.
0:36:59 So they themselves are often just wearing something that’s not very interesting.
0:37:04 So I wouldn’t judge a tailor’s work by how they dress, but I would judge a tailor’s work
0:37:07 by the customers that come out.
0:37:13 So if the customers come out and they all are wearing suits that don’t fit, the chance
0:37:16 of you getting a good suit from that tailor is very low.
0:37:22 But if all the customers walk out and their suits fit perfectly and especially helps if
0:37:25 the customers walk out or have a similar build as you.
0:37:28 So if you are a very heavy guy and you see heavy guys walking out of the store and they
0:37:33 all have suits that fit beautifully, well, then yeah, the chance of you getting a good
0:37:35 suit from that tailor is very high.
0:37:39 So you’re not going to stake out a tailor shop and like just walk see who comes out
0:37:41 the door, but you can do this on Instagram.
0:37:48 You can go to Instagram, go to the tag section and see if the people that wear their clothes,
0:37:49 if their clothes fit well.
0:37:50 Yeah.
0:37:53 I like to collect old denim.
0:37:59 So I’ve been into salvage and raw denim since probably 2008.
0:38:00 It’s kind of a weird hobby.
0:38:02 Oh, so you are not new to this.
0:38:06 If you’re into denim in 2008, you are actually, you’re very seasoned.
0:38:09 And so you know this stuff very well.
0:38:12 Denim is my, I’m an American history nerd.
0:38:13 I’m very passionate.
0:38:16 So have you ever seen a TV show, American Pickers?
0:38:17 Yeah.
0:38:19 I used to work with Mike when I was in college.
0:38:22 That was my college job was working with Mike from American Pickers.
0:38:28 And so I got, and I’m obsessed with American history and there are two or three things that
0:38:33 are very American are denim and the leather jacket.
0:38:40 And so I’ve always owned shot leather jackets or I’ve always been, or Buko leather jackets.
0:38:41 Yeah.
0:38:45 And then like red tag Levi’s or big E Levi’s.
0:38:50 I was one of the first cover customers of I’m a Gina Willie and I would spend like ungodly
0:38:52 amounts on denim.
0:38:53 And I would say I have them all saved.
0:38:57 I’ve dozens of them saved because I want to, I read Heddles and I’ve like been the
0:38:59 fate of the Fade Friday.
0:39:00 Oh man.
0:39:03 You were presenting yourself as new to this hobby.
0:39:06 You are as seasoned as they come.
0:39:11 Anyone who says all of those words, Heddles and I’m a Gina Willie and, you know, shot
0:39:12 well.
0:39:13 Mad Carrie from I’m a Gina.
0:39:16 Like I used to go to the store all the time when I didn’t have any money and they would
0:39:18 kind of pity me and give me a shirt every once in a while.
0:39:22 And then like when I started making like $10 an hour or somewhere, I would like, I bought
0:39:26 my first I’m a Gina and I would get shrink to fit Levi’s back when I was 18.
0:39:27 I love that shit.
0:39:32 But as I got bigger, I got, I’m into weightlifting and so my legs got too big for a lot of these
0:39:33 like traditional stuff.
0:39:38 So I’ve, then I used to go to self edge and SF and get a flat head.
0:39:40 That was, anyway, the Japanese shit I love.
0:39:46 And so my point being, I spent all this money on denim and what I’ve, and it’s sort of like
0:39:50 you start as a beginner where you buy cheap shit and then you go in the middle, which
0:39:53 you buy really expensive high end stuff.
0:39:59 And then now I’ve sort of ended on the other side to where I’m just buying $30 wranglers
0:40:01 that fit well.
0:40:07 And so, but like with, with, with tailoring stuff, that’s what you’ve inspired me with
0:40:08 is tailoring stuff.
0:40:13 I’m kind of new to where I’m buying the cheap shit, thrifted stuff that, that I could tailor.
0:40:15 That’s actually pretty dope.
0:40:17 But then I’m like going to like suit supply, which is like the thousand dollar shit.
0:40:20 And I’m like, it kind of sucks.
0:40:25 I should either like go to like keep the cheap dude, cheap thrifted stuff that you get tailored
0:40:26 or go like pretty high end.
0:40:32 That journey, what you’re talking about, imagine if you started that denim journey and you’re
0:40:35 buying like 21 ounce iron hearts.
0:40:36 Yeah.
0:40:39 You would probably not even get into it because you would be like, this is insane.
0:40:40 No, it’s the pain in the butt.
0:40:41 Yeah.
0:40:42 Yeah.
0:40:47 The only way that you end up buying 21 ounce iron heart denim is if you start with 14
0:40:49 ounce iron, you like how they feel.
0:40:53 And then someone says, oh, why don’t you try 16 ounce and then you, you like, you really
0:40:54 like how I feel.
0:40:56 And then you move up and all of a sudden you’re at 21 ounce and then you like, I actually
0:41:02 do like this even though it’s no sane person would ever like this, but it’s just because
0:41:04 I’m in this hobby.
0:41:08 So that’s to me the same with rated wear with tailoring is that you start, you have to figure
0:41:10 out what you like.
0:41:11 There’s a really good book that I like.
0:41:16 It’s called Perfumes, the guide by Luca Turin and Tanya Sanchez.
0:41:17 A book on perfumes.
0:41:18 Yeah.
0:41:21 But it’s just, it’s just a, it’s just a list of reviews.
0:41:25 So it’s only helpful if you, if you’re into perfumes and you want to look up a review
0:41:27 of what someone thinks of a perfume.
0:41:33 But in the introductory chapters, Tanya Sanchez writes, I’ve talked to hundreds of people
0:41:38 who are into perfumes and they all seem to follow a similar journey.
0:41:42 In the beginning, there’s this exploration stage where you’re like finding perfumes and
0:41:46 like your mother’s wardrobe or your father’s dresser or whatever.
0:41:48 And then you explore different notes.
0:41:52 And then there’s the stage where you think you’ve found your taste and you have very
0:41:56 rigid rules about everything, your very strong opinions.
0:42:01 And then the third final step is what she feels is nirvana where you know the rules,
0:42:05 but you’re not like strict about them and you just like what you like.
0:42:10 So I think that’s actually pretty true for a lot of things, whether you’re into motorcycles
0:42:15 or whether you’re into, you know, you’re a foodie or you’re into fountain pens is that
0:42:21 people start with an exploration stage, they figure out the terrain, you know, the hills
0:42:23 are over there and the lakes are over there.
0:42:27 And then they get very adamant about rules, like everything has to be this way.
0:42:31 And then there’s a point where they just know what they like and they’re not as adamant
0:42:32 about the rules.
0:42:36 And sometimes the things that they like are not even the expensive coveted things that
0:42:40 everyone talks about, it’s just something they like.
0:42:41 And that’s it.
0:42:43 That’s the emotional, that’s the nirvana that you reach.
0:42:46 So the thing that you like might just be ranklers.
0:42:51 It’s just a pain in the ass that you have to spend as much money, that much money and
0:42:54 in a decade to go through this.
0:42:57 And that’s why I mean, that’s why I like reading your blog and reading people like you is like,
0:43:02 I’m like, how can I just like speed run some of these learnings and just not make the mistakes
0:43:03 that I’ve made before?
0:43:09 Like, for example, a big thing in clothing that that a lot of people are bringing back
0:43:11 is high rise trousers.
0:43:16 And like there was this period where we went through like slim clothing.
0:43:20 And first of all, it’s the fucking worst because it looks stupid looking back on it.
0:43:26 And it’s like incredibly uncomfortable and like half the dude, half men can’t like they
0:43:28 have big asses and big thighs.
0:43:29 Like we can’t wear that stuff.
0:43:32 Like you can only wear that stuff if you’re a smaller person.
0:43:37 But it’s like, I just wish I would have like stuck to more timeless things and thought what
0:43:43 will what was cool 50 years ago and will likely be cool in 50 years from now or what I think
0:43:44 will be cool.
0:43:48 And I just wish I wouldn’t have gone through that that that slim phase because now I have
0:43:53 so much slim stuff and I’ve spent tens of thousands of dollars probably on it.
0:43:54 Yeah.
0:44:00 I mean, I will say that that high rise, fuller leg look, I often talk about online in the
0:44:04 context of tailored clothing, if you’re if you want to dress like Mick Jagger and rock
0:44:08 and roll kind of like, you know, tight leather jackets and tight rock t-shirts, then you
0:44:10 need tight pants.
0:44:14 It only works if you’re a small, if you’re a smaller person, by the way, that I don’t
0:44:16 think you have to be a very slim dude.
0:44:22 If you’re above 510 and over like 180, it’s hard to pull that off because you just look
0:44:23 like you look stupid.
0:44:26 And I’ve tried to do that and I look so dumb.
0:44:30 I do think it helps to be a certain build for that look.
0:44:32 And then the whole look has to come together.
0:44:34 You have to again, think of it in terms of like a social language thing.
0:44:38 But if you’re wearing a tailored jacket, like a suit jacket or sport coat, I do think there
0:44:42 are certain proportions for the trousers that work better for the jacket and especially
0:44:46 is works better across a wider range of men.
0:44:51 There are some men who can wear very, very skin tight suits, but they are often very
0:44:55 thin and they usually have very broad shoulders compared to the waist.
0:44:56 They’re basically models.
0:44:58 Like if you look at runway models, they’re wearing the suits.
0:45:01 They do look good, but most people are not built like that.
0:45:04 And a jacket can only be as tight as your body allows.
0:45:10 So at some point you have to figure out how to create a trouser silhouette that works with
0:45:17 the jacket that you’re wearing and the jacket is constrained by your own body’s proportions.
0:45:18 I appreciate you coming on this podcast.
0:45:21 You’re the man and thank you for everything.
0:45:22 Thank you.
0:45:23 Thanks for having me on.
0:45:24 This was such a pleasure to be on.
0:45:25 So thank you for the opportunity.
0:45:26 Thank you.
0:45:27 And that’s the pod.
0:45:28 Thank you.
0:45:29 Thank you.
0:45:30 Bye.
0:45:31 Bye.
0:45:32 Bye.
0:45:36 Bye.
0:45:37 ♪ Body ♪
Episode 649: Sam Parr ( https://x.com/theSamParr ) talks to Derek Guy ( https://x.com/dieworkwear ) about how to dress better, have more confidence, and where and how to build a wardrobe that lasts decades.
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Show Notes:
(0:00) Why it matters
(3:17) Sprezzatura
(6:01) Ralph Lauren
(9:33) Advice for the American male
(15:16) How to find a tailor
(17:21) Why we dress worse now
(20:15) How to build a wardrobe
(24:54) Budgeting
(28:23) Ready-to-wear, made-to-measure, and bespoke
(34:21) Personal style nirvana
(39:18) Buying for the decade
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Links:
• Die, Workwear! – https://dieworkwear.com/
• Inside the Mirrortocracy – https://carlos.bueno.org/2014/06/mirrortocracy.html
• The Paradox of Choice – https://www.amazon.com/Paradox-Choice-Why-More-Less/dp/0060005696
• How to Judge Quality in Clothing – https://www.putthison.com/how-to-judge-quality-in-clothing/
—
Check Out Shaan’s Stuff:
Need to hire? You should use the same service Shaan uses to hire developers, designers, & Virtual Assistants → it’s called Shepherd (tell ‘em Shaan sent you): https://bit.ly/SupportShepherd
—
Check Out Sam’s Stuff:
• Hampton – https://www.joinhampton.com/
• Ideation Bootcamp – https://www.ideationbootcamp.co/
• Copy That – https://copythat.com
• Hampton Wealth Survey – https://joinhampton.com/wealth
• Sam’s List – http://samslist.co/
My First Million is a HubSpot Original Podcast // Brought to you by The HubSpot Podcast Network // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano