Die, Workwear: "This is how to look better in your 20s and 30s"

0:00If you're a young man in your 20s and 30s and you want to be more confident, this episode is for you. And it's going to be a little strange. If you saw this headline, if you saw this title, you're going to think, why on earth is this happening on a business podcast? Today's episode is with Dye Workwear. Dye Workwear is the username of a person who's gone incredibly viral on Twitter. He has over a million followers and he talks about men's fashion. I saw this guy pop up last year and it kind of changed my life because he taught me about dress and how dressing a certain way, it gives a huge amount of confidence.

0:31And the problem is that you don't try to dress nice because you don't really know the rules. And so I thought it'd be fun to talk to Derek about his rise. So how we got huge and built the business, but also some practical tips on how to dress better and what that means for your life and what that means for your confidence. So give this episode a listen and I'll talk to you in a little bit. I feel like I can rule the world. I know I could be what I want to. I put my all in it like no days off on the road. I think the reason why you're blowing up right now, I'll give you my opinion. Maybe you could give me your opinion.

1:03But I care how I look. And I've always cared about that. But I never really knew the rules. And basically, when you don't know the rules of something, you feel not confident. And you kind of just revert back to like, well, I'm just gonna do the lazy thing of like wearing athleisure or like kind of boring clothes. But you have this line that you repeat constantly, which is clothing is a social language. And you kind of have taught people how to speak it, which kind of gives confidence. and it makes your clothing feel like armor, but also you're dressing like the person you want to be and you're speaking the language of the people who you want to speak with and kind of what you want to behave like.

1:40And I think this is why millions of men have liked you because you're giving them confidence and teaching them the language. I do think of clothing as social language and I've always thought of it in that sense because if you grew up any time before the internet, you may have been part of some social group around a hobby or an interest, like you're a skater or you're into punk music or whatever. And everyone I knew dressed a certain way to communicate an identity, like they were a jock or they're a nerd or whatever. And there was always rules around that. Look, even if no one wrote a book and spelled it out for you, you kind of knew that this was the look and everyone kind of conformed to the look of their social group and identity.

2:20And it kind of broadcasted a message. And I think over time, I've just kind of taken that idea and talked about how it's also used in classic tailoring or tech wear or whatever's the aesthetic genre. People are using dress to communicate something. And even people who dress in ways that is subconscious that they think they don't care about clothes, they still kind of dress according to their socioeconomic class. I bring up this example often. There was a moment in the tech industry in the early 2000s where the hoodies and jeans uniform was a way to signal, I don't care about clothes. I'm like the whiz kid, you know, kind of hacker that's reshaping the economy.

3:04All I care is about meritocracy and skills. But it just so happens that over time within that industry, everyone started to also dress the same. So to some degree, people are at least conscious of what is the look within their group. and they were careful to not deviate too far from it because they want to signal that they belong. There's an article that I often mention on Twitter and sometimes in interviews. The author's name is Carlos, but I can't remember his last name. But he wrote an article called Inside the Miratocracy, mirror, like looking into the mirror and the nitocracy. And his article was about how even in the tech industry where people say they don't care about clothes, everyone mirrors each other and clothes do play a part because if you showed up to a job interview for the tech industry and you wore a three-piece suit, people assume that you don't fit in and they will read something into your clothes.

3:53So to some degree, clothes do matter. This is the first time we've ever done an anonymous podcast. And I want to ask you a bit about your rise. So if there's ever anything that you just don't want to answer, just let me know. But is this your full-time gig now, which is kind of being a writer or whatever it is you describe yourself as? Yeah, I make my living off writing about menswear. There's this concept that I think I learned from you or a rabbit hole you sent me down. Is it called sprazzatura? Where it's like you're being careless, but that's kind of the cool part, right? It's like not trying too hard, but you look amazing.

4:29Did I explain that accurately? Yes, it was originally introduced by an Italian writer during the 16th, 17th century. And the writer who originally used this term was describing how to serve the king. And they were saying that you should do things in a way that conceals your effort. An easy way to understand this is like, if Sam asked me to do a favor, can you, you know, pick up my car from this location and drive it to this place? I will do the favor, but insist that it's no big deal. It's not a problem. Don't worry about it. even if it is actually kind of inconvenient. And it's a way to essentially, I guess, serve you, is to make the person feel good about what they've asked of you.

5:16But spresatura in a men's style sense is basically to dress in a way that conceals the effort that you've put in. But the concept goes way back before this writer. It goes back to even Brummel, who is largely understood to have shaped much of modern men's style. And Brummel used to spend hours tying his cravat, his white cravat, which is kind of like a neckerchief. There's a famous story, probably made up, but the story is that one of his valets was seen exiting the room once with a huge pile of cravats. And someone asked him, what are those for? And he said, these are our failures. And the idea was that Brummel actually spent hours and hours and hours in the morning putting together his look.

6:04And then he'd walk out and then pretend that he just happened to have fell into these clothes. Like it was no big deal. It was a complete natural thing. He woke up like this. And that is part of the idea that style is kind of a natural extension of you and it's not an artifice. And that's sort of, you're doing Sprezzatura with your Twitter handle and with your writing and with your reach. You're like, oh, I just kind of just wrote what came interesting. And I don't know how big it is. But in reality, you're just behind the scenes, just scheming. You're just like, oh, I just wrote this really funny burn to this guy who replied.

6:41And it just happened to get 2 million views. Because that's one of the things that you do, which is pretty funny, is you reply to a couple people, but you murder them. It's called murder with words. You just kind of annihilate them. And that's kind of your style, which I find hilarious. but one person you've turned me on to is um ralph lauren and ralph lauren has an interesting story but i'm like getting obsessed with some of his quotes because he was raised a very normal background but he said that he got obsessed with movies at a young age he was like i you know i'm not sure if i can be an actor but i can design my life via clothing you know if i put on a farmer's outfit i'll feel like a farmer if i put on a soldier style office i'm gonna feel like a soldier.

7:25I'll feel tough and brave. And he has this great quote. He says, I don't design clothes. I design dreams. And then he dresses as if whatever he wants to become. He was a Jewish kid from the Bronx. He was like, I want to feel like this like old money sophistication. So he started dressing like that and he became it. And I think that's what is interesting about what you've opened up to a lot of people is this idea of like acting as if and then you become. Yeah. If you go through a Ralph Lauren flagship, it's not true for their normal stores or normal stories or just normal stories. But if you visit a Ralph Lauren flagship, it's like walking through like Epcot Center, like the amusement parks, and there's like the pirate ship world, and there's a rocket ship world and all that.

8:02You go through a Ralph Lauren flagship, there's like the ranch world, there's the old money world, there's, you know, there's all these different worlds that he creates around costumes. And it's because he knows how to imbue you with both that fantasy and to kind of use that language and design to reference different social ideas and identities. I want to ask you practical tips on like dress and things like that. But I actually want to ask you practical tips first on learning. I've noticed that you're pretty insane. Like I read a blog where it starts off like saying in the 1959 book, Try for Elegance, which centers around men's clothing.

8:38And then you like quote the book and you tell a story about the book. And that leads into the rest of your writing. I went and tried to find that book. That was a book that's out of print. That's like$300 or something like that. And it has like no reviews on Amazon. And then you'll do like the history of Tweed. And I'm like, how the hell do you know this shit? And so what I want to know is how are you learning all these things and storing the knowledge? That's what fascinates me about you is like your mastery of a topic. That comes with a lot of buying stuff that ends up being crappy. So I've bought a lot of books on clothing.

9:16If they're, you know, especially old books. and if it was published in some, you know, sometime, and it was this obscure book, I'd buy it and then read it. And a lot of that stuff ends up being crappy. But sometimes there's like a nugget. Over time, I think you get a better sense of like which books to buy. Obviously, you're not just constantly doing the scattershot. But I do end up buying a lot of books and then reading them. And then sometimes there's like a nugget here and there. It does help, I would say, that fashion as a topic for a while was not treated seriously. And then to the degree it is treated seriously, it's often focused on women's clothing.

9:49And then to the degree that men's clothing is taken seriously, there are many brilliant academic writers who focus on men's clothing, but they tend to be extremely academic. So I am in a space where I'm just enthusiast and I try to write something that ties clothing into other parts of culture, which I hope makes it more interesting to everyday people. And I try to do something that's a little bit smarter than just like basic trend reporting or fashion writing, but it's a little bit more accessible than academic writing. And then I also tread this water where not a lot of people are treading. And I think that kind of helps.

10:27I think it helps to be in this very specific space. Today, you had a thing about like the quarter zip and like that caused so much, so much outrage. And I think I said you were coming on. I got so many people that are pissed off that you were coming because they were like, Dude, he's so unrelatable to the middle America guy. And I think though that oddly, those people are folks that are being turned on to right now. What are the common issues that they come to you with? And what's the general advice to the three most common things for like, if you do this, this, and this, you're going to be 60 % of the way there or significantly better.

11:04You can't answer any of those things without first thinking of closed a social language and the thinking of what you want to communicate. So if you think of closed a social language, you are, to me, like 90 % of the way there. Because then you can think of like how something should fit and the colors and the styles and all that combined. I admit that as my account has grown, I've leaned a little bit more towards tailoring. Before my account started growing, I talked about a much wider range of styles, often like Japanese workwear or something. And I've leaned a little bit more into tailoring because that's an aesthetic language that I think more people understand.

11:34Is that limited to suits? Suits, sport coats, anything that would be considered like maybe smart casuals. I think there are certain kind of aesthetics that like everyone recognizes, oh, that's good. Again, bringing it back to language, if you think of like dialects, received pronunciation, everyone recognizes that as like the quote unquote correct pronunciation. And they recognize that as the good English. But, you know, throughout the UK, there are many dialects. And even though everyone recognizes received pronunciation as the dialect, if you speak received pronunciation in certain parts of England, you might come off as kind of crazy because everyone there speaks in a different dialect.

12:15But if you take that dialect and put it across the nation, a lot of people are going to be very opinionated on whether or not that is the correct way of speaking because that's very regional. So there are certain modes of communication that are hegemonic and suit, sport coats, a certain kind of like dressy kind of look is what I would consider hegemonic in visual aesthetics. even though wearing a chore coat or wearing a punk rock biker jacket or other aesthetics can be legitimate in their own way. It's just that if you present that to other people, it's more controversial and fewer people are going to recognize it as quote unquote good because it's so regional.

12:57The problem with, I will admit when you're talking about like the Midwestern guy, I get this a lot, is that somebody from outside of San Francisco or New York City or Los Angeles to say, I really like what you put out there. How can I dress like this? And that is sometimes a question I can't answer because if you want to wear sport coats and you live outside of a handful of cities, and especially if you fall outside of, you know, straight sizing, let's say you're a size 46 chest. I just got an email the other day. Someone has a 48 chest, but a 32 waist. They're a professional baseball player. If you're that build and you are outside of the major cities, I don't really have an answer for you because tailoring has died over the last few decades.

13:44There aren't many good tailors. So what you're going to find is a lot of ready-to-wear tailoring, which is not going to fit an unusual build. And then you also have to be the kind of guy that's willing to wear a sport coat, even though other people aren't wearing a sport coat. you have to put up with the fact that you are overdressed and you're doing it for yourself and it's pleasing to you. So sometimes if you're in a smaller city, there may not be a lot of options and there may be, I think, harsher judgments. Whereas I think in a big city, you have a certain kind of anonymity where you can dress very different from others and nobody cares.

14:23Like nobody cares if you arrive to the office in a support code and everyone's dressed down. I still think you can in a small city. I have a friend who works for a religious organization. He lives just outside of Nashville. Yeah. Men musing, gentlemen musing. Yeah. Men's wear musings, Matt Mitchell. Yeah. He works for a religious organization and he wears a sport coat with jeans to the office. He told me that nobody in his office wears tailored clothing except for the really old guys. But he does it so often now that that's just like him. And one, he's obviously not going to get fired for it. But two, it's not like anyone comments on it anymore.

15:01It's just him. And I think it does take that kind of personality. And it takes a willingness to really hunt for those ready-to-wear pieces to figure out how things fit. Because historically, men dressed well in tailored clothing, not because they knew all of this stuff. It's because they went to a local clothier and that clothier like outfitted them. They, you know, you'd go to your clothier and you'd say, I have to go to a summer wedding or I work in this office, like just figure out how am I supposed to dress? And that clothier told you, you're going to summer wedding. This is the thing that you're supposed to wear.

15:33And they'd figure out how it's supposed to fit. And they do all the tailoring and all that. And you walk out and you look amazing. Those clothiers have disappeared and customer loyalty is no longer there as well. So whereas a man used to go to his tailor and would introduce his son to his tailor. Now men shop from different places, not only different aesthetics, but they might buy their jeans from a jean company, shirts from a shirt company, socks from a sock company. Sometimes they're also buying the stuff online where there's no sales associate to guide them. And then they have to figure out how to put together not only a good outfit, but also a good wardrobe and how to use that wardrobe to move throughout different social spaces.

16:15All right, you're telling me this and I'm like, all right, I'm bought into all that, but I feel hopeless. So I live right outside of New York City, so it's okay for me. I can go to New York City, but I still feel hopeless where I'm like, this sounds super intimidating finding a tailor. Yeah, there are solutions depending, everyone has to figure out their own specific situation. If you're the guy that emailed me recently, he's a baseball player, 48 chess, 32 waist, you are absolutely not going to find anything in ready to wear or made to measure. You have to go to Bespoke Most people are not that build.

16:44Most people are not professional baseball players. Most people are actually pretty average size, so they can usually get a good enough fit and ready to wear. I have some articles on, you know, where I think you can shop for a suit, but the issue is still that the effort is put on you. You have to figure out what are your fit issues? How do you want to dress? How to put together a wardrobe? Someone recently emailed me with photos of a poet. This person's writing an article about this poet's life and this poet lived Somewhere on the East Coast. Early in this poet's life, there was photos of him as a young person, I would say like in his 20s or so in the 1930s.

17:21And then over time, you see him in the 20s and 30s. He dressed really, really well, exceptionally well. I mean, average for the time, but looking back, like very, very well. And then over time, his dress started to worsen. And as I was explaining to this writer, if you can imagine this poet has an interest level in clothing, we'll say 70 out of 100. In the 1920s and 30s, he just has to walk down the block to get whatever he needs. And then over time, as tailoring disappears, it's harder to find good clothiers. And the number of options balloons, and there's all these different languages. A level 70 is only going to get you so far.

18:04Your interest level has to be 90 or 95 to get to how he dressed in the 20s and 30s because now you have to source things online. You have to do all this crazy work. There's a lot of burden now on the consumer, which is partly why it's difficult to build a wardrobe. It doesn't mean that another, a podcaster interviewed me once and they asked, do you feel that most people are badly dressed? And that's a very loaded question because I think there are many well-dressed people if you understand their own dress aesthetic and language. when I walk around San Francisco, I see people wearing cool hiking gear or vintage gear, but they're often like embedded in some kind of cultural community.

18:43But if you're outside of a cultural community that doesn't have much cultural capital, because that's, in my view, how we think of aesthetics, we think of in terms of cultural capital and social language. If you're outside of those communities and you're not a punk and you're not a cool hiker or you're not part of a rock band or whatever, then you kind of have to figure out where to buy the clothes that express an identity that you like and how it should fit and all of that. And yeah, it's unfortunately a much harder uphill battle than it was 50 years ago. There's a really good, he used to teach business at University of California, Berkeley.

19:19I don't know if he still does. His name is Barry Schwartz and he wrote a book called The Paradox of Choice. That book opens with a story of how Schwartz enters the gap and is shopping for a pair of jeans. And the sales associate asked him, do you want washed, raw, rinsed, white, dark, blue, slim fit, slim straight, tapered, you know, baggy, athletic cut? And he gave him all these options. And he said he walked out that day from the gap with the best pair of jeans he's ever bought, but he was left more unsatisfied than he's ever felt because just knowing that there are so many choices made him question the choice that he made that day.

20:00And part of his book is that people are often better off if they're given a much more constrained number of choices. So if you think of like going into an Apple store, there are very few choices and they've constrained it to make the purchasing decision process easier. But they are, I mean, presumably they think so. They're all good choices. And the problem at the moment at the market is that there are billions of choices for any style of item, following any number of design languages, any number of fits, and that has caused incredible anxiety in the market, which is very difficult to solve. Here's how I'm solving it, is I go to your blog or people who I like or follow on Instagram and I'm just like, I'm just going to do what they do.

20:42And it's sort of like when you learn how to play music, you play other people's music for a long time and then you start feeling like, man, I love this little riff from this rock, genre. And then I'm inspired a little bit by this thing. And I start crafting my own because I've just learned the technique. And I know what's cool and what's not and what's my texture. With dress, it's the same thing where it's like, all right, I'm new. So whatever Derek or whoever I follow on Instagram does, I'm just going to copy that. And in doing that, after a couple years, I'm going to develop my own sense. And so the question I have for you, which is, it's hard to know when you're shopping online, which is what I think most people in their 20s 30s do, it's hard to know what's good.

21:25And the reason why you need to know what's good is because if I were to follow what you and a lot of people say, I would be buying so much stuff. But that's not exactly what you're wanting me to do. I think what you and what I believe is that you should buy for life. You buy less things, but you buy high quality things that can last a lifetime. I still struggle to figure out what those high quality things are. And so my question is, how should I figure out what is a high quality brand or high quality product that is deserving of more money to be spent online? Yeah, I agree with everything you said of find people that you like and copy them.

22:05On the issue of how to find the quality thing. It sounds like you've read a lot of my work. So I've written about different ideas of how we think of quality. There's the build quality. So there is such a thing as a certain kind of build quality with clothes. So to give an example, leather dress shoes. If you buy leather dress shoes made with a Blake stitch or Goodyear welt on the sole and the uppers are made from full green leather, those shoes will age better, last longer, and they can be resold. Like an Alden. Yeah, like an Alden. Versus if you buy something with a glued on sole and made from corrected green leather, that corrected green leather is a bad leather that's been sanded down to remove the blemishes or scars and whatnot and then coated with some chemical to make it look smooth and normal again uniform and that coating eventually flakes off doesn't age very well so you end up looking at your shoes and you don't like how they look and then you go out and buy a new pair whereas full green leather will age better over time it will look more natural it gets the kind of patina that people like and then with a stitched on sole you can always unstitch the sole and replace it you can actually still replace glued on soles, but it's a little bit more risky.

23:19There's only so many times you can do it. And I wrote an article and put this on how to judge quality in clothing. And it runs through almost all of the categories. I mean, you know, except, except for like Gore-Tex parkas. I mean, generally speaking, sweaters, shoes, tailored jackets, you know, like woven shirts, things like that, like how to think of quality. but the scope of build quality is actually pretty narrow. There are some things that are generally agreed upon as what is good build quality. To give an example, with tailored jackets, there are certain kind of ideas of what is the better or worse tailored jacket in terms of build quality, but some things are pretty subjective.

23:56And if a designer is trying to bring a suit or sport coat to market, they're working with a factory and that factory has, let's say, like 300 operations, there is a certain gold standard for quality, quote unquote, but a designer is often not trying to sell like a five, six,$7 ,000 suit. They're trying to sell a$2 ,000 suit. So they have to make design decisions on where to cut back, quote unquote, and how they decide which part of those 300 operations to cut back is more is I think very subjective but the real measure of quality should be are you excited to put it on today and do you think you'll be excited to put this on 10 years from now that doesn't always mean wearing a classic aesthetic it could be mean wearing something crazy because you like wearing crazy clothes and then will this thing last to you know some degree there is there is like a certain kind of build quality in terms of will this thing last?

24:58If you buy something and it falls apart in two years, I think most people would want something that lasts a little bit longer than that, like as a physical item. So I think those things, do you get excited wearing it? Will it last design-wise and also kind of construction-wise? And then also, does it fit and flatter you? When you put it on and you look at yourself in the mirror, do you like how you look? And I think those basic points, are you excited by the thing that you're wearing and does it fit and flatter you, I think gets you much further than thinking of this purely as an engineering problem.

25:34You can't just read specs off a sheet like when you're buying electronics. To some degree, it's more like food. When you bite into it, does it taste good? Are you excited to go out to that restaurant? I think that's a much more, a better way to approach things. It's a more holistic way to approach things than thinking of it just in terms of, is this well-made? When I was kind of up and coming in my career, I didn't have a lot of money and I started my own business and didn't pay myself very much. And so I was afraid to spend and buy things, even though I wanted stuff. But even after I made a little bit of money, I was still always nervous to spend.

26:10And so I see guys like you, these writers who I admire, and they've got some great clothing. And in my head, I'm wondering, how many items do they actually own in their closet? and how many like because like up until recently i could have gone six months without buying a clothing item now i'm like you know i think on your blog you say when you first get into this shit even if you have money buy slow ease into it a little bit and i'm like pulling myself back because i'm like oh i want to get this and i can afford it and so i'm like i want all this shit how many things do you buy per month and what's like a reasonable uh amount of spend do you think for someone who can afford these things.