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

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. — 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 — 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

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Sam Parr?

  If you're a young man in your twenties and thirties and you want to be more confident, this episode is for you. And it's gonna be a little strange. If you saw this headline, if you saw this title, you're gonna think, why on earth is this happening on a business podcast? Today's episode is with Di Work Wear. Di Work Wear 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. And 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 he got huge and built a business, but also some

• 0:42Sam Parr?

  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.

• 0:58Sam Parr?

  I think the reason why you're blowing up right now, I'll give you my opinion and maybe you could give me your opinion, but 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 you want to speak with and kind of what you want to behave like. And I think this is why millions of men

• 1:41Sam Parr?

  have liked you because you're giving them confidence and teaching them the language.

• 1:45Speaker 01

  I do think of clothing as social language and I've always thought of it in that sense because, you know, if you grew up anytime before the internet, you know, 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 were 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. And it kind of broadcasted a message. And I think over time, I've just kind of taken that idea

• 2:27Speaker 01

  and talked about how it's also used in classic tailoring or, you know, tech wear or whatever's the aesthetic genre. People are using dress to communicate something. And even people who dress in ways that the subconscious that they, 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. All 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.

• 3:11Speaker 01

  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 a, 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 thenocracy. And, 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. So to some degree, clothes do matter.

• 3:56Sam Parr?

  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?

• 4:12Speaker 01

  Yeah, I make my living off writing about menswear.

• 4:15Sam Parr?

  There's this concept that I think I learned from you, or a rabbit hole you set me down. Is it called sprezzatura? 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. Did I explain that accurately?

• 4:31Speaker 01

  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.

• 5:17Speaker 01

  But sprezzatura, 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

• 6:02Speaker 01

  in the morning putting together his look. And 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.

• 6:20Sam Parr?

  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, you're like, oh, I just wrote this, this really funny burn to this guy who replied. And it just happened to get 2 million views. Cause that's what, one of your, the things that you do, which is pretty funny is you like, reply to a couple of people, but you murder them. Like it's called murdered with words. You just kind of annihilate them. And that's kind of your, your style, which I find hilarious. But one person you've turned me on to is Ralph Lauren.

• 7:02Sam Parr?

  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 going to feel like a soldier. I'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, 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,

• 7:46Sam Parr?

  acting as if, and then you become.

• 7:48Speaker 01

  Yeah. If you go through a Ralph Lauren flagship, it's not true for their normal stores. Their normal stores are just normal stores, but if you visit a Ralph Lauren flagship, it's like walking through like Epcot Center, like amusement parks. And there's like the pirate ship world and there's a rocket ship world and all that. You 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.

• 8:21Sam Parr?

  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. And 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 of these things and storing the knowledge?

• 9:03Sam Parr?

  That's what fascinates me about you is like your mastery of a topic.

• 9:07Speaker 01

  That comes with a lot of buying stuff that ends up being crappy. So I've bought a lot of books on clothing. If they're, you know, especially old books. And if it was published in some, you know, some time and it was this obscure book, I'd buy 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.

• 9:49Speaker 01

  And 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 is 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. I think it helps to be in this very specific space.

• 10:31Sam Parr?

  Today you had a thing about like the quarter zip. And like that caused so much, so much outrage.

• 10:38Sam Parr?

  And I think I said you were coming on. I got so many people there 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 the common issues that they come to 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?

• 11:04Speaker 01

  You can't answer any of those things without first thinking of clothes as social language and the thinking of what you want to communicate. So if you think of clothes as 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 to combine. I admit that as my account has grown, I've leaned a little bit more towards tailoring. Before my account started to grow, 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.

• 11:34Sam Parr?

  Is that limited to suits?

• 11:36Speaker 01

  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 that's good. Again, bringing back to language, if you think of like dialects, received pronunciation, everyone recognizes that as like the quote unquote correct pronunciation and they recognize 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. But if you take that dialect and put it across the nation,

• 12:20Speaker 01

  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 suits, 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 a fewer people are going to recognize it as quote unquote, "good" because it's so regional. The problem with, I will admit, when you talk about like the midwestern guy, I get

• 13:01Speaker 01

  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. There aren't many

• 13:45Speaker 01

  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. Like, nobody cares if you arrive to the office in a sport coat and everyone's dressed down. I still think you can, in a small city. I have a

• 14:30Speaker 01

  friend who works for a religious organization. He lives just outside of Nashville.

• 14:35Sam Parr?

  Yeah, Men Musing, Gentlemen Musing?

• 14:38Speaker 01

  Yeah, Men's Wear Musings, Matt Mitchell.

• 14:40Sam Parr?

  Yeah.

• 14:41Speaker 01

  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, it'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

• 15:25Speaker 01

  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 some wedding, this is the thing that you're supposed to wear. And 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,

• 16:08Speaker 01

  but also a good wardrobe and how to use that wardrobe to move throughout different social spaces.

• 16:15Sam Parr?

  All 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.

• 16:28Speaker 01

  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 chest, 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. Most people are not professional baseball players. Most people are actually pretty average size, so they can usually get a good enough fit in 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.

• 17:11Speaker 01

  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 twenties or so, in the 1930s. And then over time, you see him in the twenties and thirties. He dressed really, really well, exceptionally well. I mean, average for the time, but looking back, like very, very well. Yeah. 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.

• 17:55Speaker 01

  And the number of options balloons and there's all these different languages. A level 70 is only going to get you so far. Your interest level has to be 90 or 95 to get to how he dressed in the twenties and thirties. Because now you have to source things online and 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,

• 18:39Speaker 01

  but they're often like embedded in some kind of cultural community. But 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. I don't know if he still does.

• 19:21Speaker 01

  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 asks him, do you want washed, bra rinsed, white, dark blue, slim fit, slim straight, tapered, 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. And part of this book is that people are often better off if they're given a much more constrained number of choices.

• 20:06Speaker 01

  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.

• 20:35Sam Parr?

  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. And, and, and it's sort of like when you learn how to play music, you play other people, you play other people's music for a long time. And then you start feeling like, man, I love like this little riff from this rock like genre. And then I like, 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 like what's cool and what's not and what's my texture. With dress, it's kind of 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 of years, I'm going to develop my own sense. And then so like the question I have for you, which is it's hard to know when you're shopping

• 21:19Sam Parr?

  online, which is what I think most people in their 20 and 30s do, it's hard to know what's good. And 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?

• 22:00Speaker 01

  Yeah, all I agree with everything you said of find people that you like and copy them. On the issue of how to find the quality thing. So there are, 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.

• 22:35Sam Parr?

  Like an Alden?

• 22:37Speaker 01

  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, 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. There's only so many times you can do it.

• 23:21Speaker 01

  And I wrote an article on Put This On: How to Judge Quality in Clothing. And it runs through almost all of the categories. I mean, you know, 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. And if a designer is trying to bring a suit or sport coat to market,

• 24:01Speaker 01

  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 $5,000, $6,000, $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, 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?

• 24:45Speaker 01

  That doesn't always mean wearing a classic aesthetic. It could mean wearing something crazy because you like wearing crazy clothes. And then, will this thing last to some degree? There is like a certain kind of build quality in terms of will this thing last? If 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?

• 25:28Speaker 01

  I think gets you much further than thinking of this purely as an engineering problem. You 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?

• 25:53Sam Parr?

  When I was kind of up and coming in my career, I didn't have a lot of money. And, uh, you know, I started my own business and like didn't pay myself very much. And so I was like afraid to, to spend and buy things, even though I like wanted stuff, you know, I was. But even after I made a little bit of money, I was still always nervous to spend. And so I see guys like you, um, you know, these writers who I, who I admire. And they've got like some great clothing. And in my head, I'm wondering, how many items do they actually own in their closet? And how many like, cause 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,

• 26:35Sam Parr?

  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 could 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 amount of spend, do you think for someone who can, can afford these things?

• 26:54Speaker 01

  Well, I do spend a lot more than the average person. I admit that. I don't know the exact number, but to give an example, I recently bought a hoodie from Bear Knuckles. I bought two double RL flannel shirts.

• 27:06Sam Parr?

  Double RL flannel shirt is what? Two to 400?

• 27:10Speaker 01

  No, I wouldn't. I would never have bought a $400 flannel shirt. I think I spent, I want to say like 175. I bought a pair of Bryson Cargo pants. Those were kind of expensive. Those were like 350. But I've been lusting over them for like a year, so I finally just bought them.

• 27:30Speaker 01

  That's for this season. I don't really imagine myself buying much for the rest of the season. So, you know, I think most people are not buying two shirts, a hoodie and a pair of pants twice a year because I break up my shopping into seasons. Spring, summer, fall, winter. And then I do use a lot of custom tailors and I usually have like a suit or sport coat in the works through a custom tailor. And that's been true for a while. So, you know, again, most people are not doing that.

• 27:58Sam Parr?

  Those suits are getting tailored? Are those bespoke or are those off the rack that you're getting fitted to you?

• 28:03Speaker 01

  They are bespoke.

• 28:04Sam Parr?

  That's interesting. That has always intimidated me because it seems like it's a it's a pain in the ass of a process. And according to your, you have one post on your blog. You're not sure if you can even tell the difference all the time.

• 28:16Speaker 01

  Yes. I had this friendly argument with a good friend of mine who strongly feels that you can tell. I will say I was in a DM, I am, I am in a DM with some guys who are into clothing. And we were looking at a politician's suit and we all suspect that he's wearing bespoke because of the stitching and the styling and all that. And we can, and we can kind of pinpoint the region of where the tailor's from.

• 28:40Sam Parr?

  But potentially that this person's wearing like $5,000 suits is what you're saying?

• 28:45Speaker 01

  No, I would, I would estimate that their suit probably cost around 3,000 to 4,000. And then I checked their Twitter account and they follow me. So I was like, maybe they do buy bespoke suits. So maybe you can tell, but I am still very skeptical of whether or not, generally speaking, you can tell the difference between ready to wear and bespoke. And I completely agree. I think bespoke is a huge hassle. There's more misses than people let on online. I think it's very important when you go into that space to know that like not all commissions turn out well. And it's often pretty common that commissions turn out poorly, even if you're using a good tailor, but there are a lot of bad tailors. One, there are some people who need bespoke.

• 29:24Sam Parr?

  We have to define it. Is the terminology like off the rack? And then one up from that is like made to measure, which is I guess a suit supply and then is bespoke purely from scratch?

• 29:35Speaker 01

  Well, the short answer then is ready to wear is what you go into store and can touch and feel and put on yourself and put back on the rack. Made to measure is something that has a block pattern, which is a pre-made pattern that they adjust given your measurements. You're measured and then they adjust the pattern, make the garment straight to finish. And then you come in for what they call one fitting, which means they put the garment on you and they figure out, you know, what needs to be changed. That fitting is basically not that much different than putting on a ready to wear garment and they do adjustments. The only sometimes difference is that in a made to measure garment, they have more inlay, which means there's more room for adjustment. And then bespoke theoretically is that the pattern is produced from scratch.

• 30:18Speaker 01

  And then there's a series of fittings, typically three, basted forward and final fitting. And then it's sort of like you can imagine it as someone sketching. Like when you're, you know, when I was in art class in high school, they taught us like do a sketch and then you kind of like fill it in and then you kind of work it out. A fitting is sort of like that. The tailor sketches out what they think is going to look good and then does a fitting and figure out what adjustments needs to be made. And then through that iterative process, supposedly you wind up with a better garment. Reality is a little bit more complex than that, but that is, that's the general contours.

• 30:52Sam Parr?

  But your recommendation is for most people, is it ready to wear and that you get tailored?

• 30:59Speaker 01

  Absolutely ready to wear because few reasons. One is that most people are straight sized, meaning they can fit into a ready to wear garment because those garments are made for the average sized person. And then two, the tiny differences, you're probably not as obsessed as I am with like, oh, like the quarters are not open enough and like the shoulders, you know, you probably are not like obsessed over those things. Even if you are obsessed with those things, you have to like realize that like 99% of people seeing you are not going to see those things. And even if they do see those things, you have to be standing like a robot for someone to spot those things. In real life, you move around and you're sitting and you're interacting with the world. So like all of the things that people are talking about, including me, those disappear.

• 31:44Speaker 01

  And then the third thing is that most people don't care about the craft element. And even if they do think they care about the craft element, they probably can't even spot it. So like, can you tell the difference between a machine-made buttonhole and a handmade buttonhole?

• 31:56Sam Parr?

  No, of course not. Very few people can, I think.

• 31:59Speaker 01

  Yeah, so like, there are some people who need bespoke, and those are people, like John Fetterman will never be able to fit into an off-the-rack garment, or even made to measure, because he's very far from the average-sized person. He would have to go bespoke if he wanted a suit that fit. But most people are not that person. And the most important reason, the top-tier reason of why everyone should try ready-to-wear first is because you can try on the garment and put it back on the rack. Nothing happens at the end of the day. Whereas with a custom garment, if the tailor offers you a money-back guarantee, they're not a good tailor. No good tailor will ever offer that, because it takes a lot of time, effort, and money to produce a good suit. And then if it's final sale, that means that if you put it on,

• 32:45Speaker 01

  it might not fit well. There's no guarantee that's gonna fit well. But even if it does fit well, you might not like the silhouette. You might have chosen a crappy fabric. Maybe you ask for dumb details, and then all of a sudden the garment's produced, and you look at it and you realize, oh, this actually looks horrible. There are many things that can go wrong. And then at that point, you've just spent anywhere from, you know, like $2,000 to $8,000 possibly for a garment, and you can't return it. Whereas with a ready-to-wear garment, you can try on a $10,000, I don't even know if $20,000 suits exist for ready-to-wear, but if they did, you could try it on and put it back on the rack, and nothing happens. And that's the number-one reason. Even if you are just getting into this, and you suspect

• 33:29Speaker 01

  that you need a custom garment, I still think you should try ready-to-wear, because when you try ready-to-wear, you can start to identify certain things. You can start to say, oh, I actually don't like how I look in a very soft-shouldered jacket. I think I need more padding. Or I don't actually like how I look in a three-button jacket. I think I want a two-button jacket. And once you start getting an eye for that silhouette, you can then start to find a tailor. Because if you know that you want a very padded cut, that narrows your options.

• 34:01Sam Parr?

  I have a tailor now and I don't know if I like it like it's kind of funny. First of all, a lot of tailors, is it a red flag if your tailor dresses poorly or has poorly fitting clothes? Or is it like one of those things where it's like the cobbler's kids is the last kids to get shoes? You know what I mean?

• 34:17Speaker 01

  Yeah, it's the cobbler's kids is the last kid. There are many tailors who who also dress poorly because many tailors are better thought of as technicians. They're not like stylists, so they themselves are often just wearing something that's not very interesting. So I wouldn't judge a tailor's work by how they dress, but I would judge a tailor's work by the customers that come out. So if the customers come out and they all are wearing suits that don't fit, the chance of you getting a good suit from that tailor is very low. But if all the customers walk out and their suits fit perfectly, and especially helps if the customers walk out have a similar build as you. So if you are a very heavy guy and you see heavy guys walking out of the store and they all have suits that fit beautifully,

• 35:02Speaker 01

  well, then yeah, the chance of you getting a good suit from that tailor is very high. Obviously, you're not going to stake out a tailor shop and like just, you know, like walk, see who comes out the door. But you can do this on Instagram. You can go to Instagram, go to the tag section and, you know, see if the people that wear their clothes, if their clothes fit well.

• 35:21Sam Parr?

  Yeah, I like to collect old denim. So I was, I've been into salvage and raw denim since probably 2008. It's kind of a weird hobby.

• 35:32Speaker 01

  Oh, so you are not new to this. If you, if you're into denim in 2008, you are actually, you're very seasoned and so you know this stuff very well.

• 35:40Sam Parr?

  Denim is my, I'm, I'm, I'm an American history nerd. I'm very passionate. So have you ever seen that TV show, American Pickers?

• 35:47Speaker 01

  Yeah.

• 35:48Sam Parr?

  I used to work with Mike when I was in college. That was my college job was working with Mike from American Pickers. And so I got, and I'm obsessed with American history. And there are two, two or three things that are very American are denim and the leather jacket. And so I've always owned shot leather jackets or I've always worn that or Buco leather jackets.

• 36:12Speaker 01

  Yeah.

• 36:12Sam Parr?

  And then like red tag Levi's or Big E Levi's. I was one of the first customers of Imogen Willie and I would spend like ungodly amounts on denim. And I would say, I have them all saved. I have dozens of them saved because I want to, I read Hettles. And I've like been the fade of the fade Friday.

• 36:31Speaker 01

  Like, oh, man, you were, you were presenting yourself as new to this hobby. You are as seasoned as they come. Anyone who says all of those words, Hettles and Imogen Willie and you know, shot.

• 36:42Sam Parr?

  Well, Matt Carey from Imogen, like I used to go to the store all the time when I didn't have any money. And they would kind of pity me and give me a shirt every once in a while. And then like when I started making like $10 an hour or somewhere, I would like, I bought my first Imogen and I would get shrink to fit Levi's back when I was 18. I love that shit. But as I got bigger, I'm into weightlifting and so my legs got too big for a lot of these like traditional stuff. So I've then, I used to go to Self Edge in SF and get a flathead. That was, anyway, the Japanese shit I love. And so my point being, I spent all this money on denim. And what I've, and it's sort of like you start as a beginner where you buy cheap shit. And then you go in the middle, which you buy really expensive, high end stuff.

• 37:25Sam Parr?

  And then now I've sort of ended on the other side to where I'm just buying $30 wranglers that fit well. And so, but like with, with, with tailoring stuff, that's what you've inspired me with is tailoring stuff. I'm kind of new to where I'm buying the cheap shit, thrifted stuff that, that I could tailor. That's actually pretty dope, but then I'm like going to like suit supply, which is like the $1,000 shit. And I'm like, it kind of fucking sucks. Like I should either like go to like, keep the cheap, dude, cheap thrifted stuff that you could tailor or go like pretty high end.

• 37:58Speaker 01

  That journey, what you're talking about, imagine if you started that denim journey and you're buying like 21 ounce iron hearts.

• 38:07Sam Parr?

  Yeah.

• 38:07Speaker 01

  You would probably not even get into it because you'd be like, this is insane.

• 38:11Sam Parr?

  The pain in the butt.

• 38:12Speaker 01

  Yeah, the only way that you end up buying 21 ounce Ironheart denim is if you start with 14 and you like how they feel and then someone says, oh, why don't you try 16 ounce? And then you like, you really like how that feel and then you move up and all of a sudden you're at 21 ounce and then you like, I actually do like this, even though no sane person would ever like this, but it's just because I'm in this hobby. I, so that's to me, the same with rated where with tailoring is that you start, you have to figure out what you like. There is a really good book that I like, it's called Perfumes, The Guide by Luca Turin and Tanya Sanchez. A book on perfumes? Yeah, but it's just, it's just, it's just a list of reviews. So it's only helpful if you, if you're into perfumes and you want to look up a review

• 38:56Speaker 01

  of what someone thinks of a perfume. But in the introductory chapters, Tanya Sanchez writes, I've talked to hundreds of people who are into perfumes and they all seem to follow a similar journey. In the beginning, there's this exploration stage where you're like finding perfumes in like your mother's wardrobe or your father's dresser or whatever. And then you explore different notes and then there's the stage where you think you've found your taste and you have very rigid rules about everything. You have very strong opinions. And then the third final step is what she feels is Nirvana, where you know the rules, but you're not like strict about them and you just like what you like.

• 39:36Speaker 01

  So I think that's actually pretty true for a lot of things, whether you're into motorcycles or whether you're into, you know, you're a foodie or you're into fountain pens, is that people start with an exploration stage, they figure out the terrain, you know, the hills are over there and the lakes are over there. And then they get very adamant about rules, like everything has to be this way. And then there's a point where they just know what they like and they're not as adamant about the rules. And sometimes the things that they like are not even the expensive. Coveted things everyone talks about is just something they like. And that's it. That's the emotional, that's the nirvana that you reach. So the thing that you like might just be Wranglers.

• 40:17Sam Parr?

  It's just a pain in the ass that you have to spend as much money, that much money and a decade to go through this. And that's why, I mean, that's why I like reading your blog and reading people like you is like, I'm like, how can I just like speed run some of these learnings and just not make the mistakes that I've made before? Like, for example, a big thing in clothing that a lot of people are bringing back is high-rise trousers. And like, there was this period where we went through like slim clothing. And first of all, it's the fucking worst because it looks stupid looking back on it. And it's like incredibly uncomfortable and like, half the dude, half of men can't, like, they have big asses and big thighs.

• 40:59Sam Parr?

  Like, we can't wear that stuff. Like, you can only wear that stuff if you're a smaller person. But it's like, I just wish I would have like stuck to more timeless things and thought, what was cool 50 years ago and will likely be cool in 50 years from now? Or what I think will be cool? And I just wish I wouldn't have gone through that slim phase because now I have so much slim stuff and I've spent tens of thousands of dollars probably on it.

• 41:26Speaker 01

  Yeah. I mean, I will say that that high-rise fuller leg, look, I often talk about online in the context of tailored clothing. If you're, if you want to dress like Mick Jagger in rock and roll, kind of like, you know, tight leather jackets and tight rock t-shirts, then you need tight pants.

• 41:41Sam Parr?

  That only works if you're a small, if you're a smaller person, by the way. That, I don't think I can.

• 41:46Speaker 01

  You have to be a very slim dude.

• 41:48Sam Parr?

  If you're above 5'10" and over like 180, it's hard to pull that off because you just look like, you look stupid. And I've tried to do that and I look so dumb.

• 41:58Speaker 01

  I do think it helps to be a certain build for that look. And then the whole look has to come together. You have to, again, think of it in terms of like a social language thing. But if you're wearing a tailored jacket, like a suit jacket or sport coat. I do think there are certain proportions for the trousers that work better for the jacket and especially is, works better across a wider range of men. There are some men who can wear very, very skin tight suits, but they are often very thin and they usually have very broad shoulders compared to the waist. They're basically models. Like if you look at runway models, they're wearing those suits. They do look good, but most people are not built like that. And a jacket can only be as tight as your body allows. So at some point, you have to figure out how to create a trouser silhouette that works with the jacket that you're wearing.

• 42:43Speaker 01

  And the jacket is constrained by your own body's proportions.

• 42:48Sam Parr?

  I appreciate you coming on this podcast. You're the man and thank you for everything.

• 42:53Speaker 01

  Thank you. Thanks for having me on. This was such a pleasure to be on. So thank you for the opportunity.

• 42:57Sam Parr?

  Thank you. And that's the pod.