Transcript: ‘The menswear guy’ on why clothing matters

This is an audio transcript of the Life and Art from FT Weekend podcast episode: ‘‘The menswear guy’ on why clothing matters’

Rob Armstrong
Welcome to Life and Art from FT Weekend. I’m Rob Armstrong, the US financial commentator at the FT and host of the Unhedged podcast. I also moonlight as a menswear columnist and today I’m in for Lilah Raptopoulos.

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If you were on Twitter in 2022, you might have noticed something odd about your feed. Just after Elon Musk acquired the platform, its new algorithm started suggesting tweets about menswear to lots of people. Lots and lots of people. The tweets were written by Derek Guy, and they and he became such a phenomenon that people were joking that Musk’s Twitter was going to be just about menswear. In the meantime, Derek, who runs the blog Die Workwear, has picked up a cool million followers on the platform. As Twitter morphed into X, he became known simply as the menswear guy. Derek is with us today to talk about men’s fashion. Derek, hi and welcome to the show.

Derek Guy
Thanks so much for having me on.

Rob Armstrong
For someone who is extremely online, you’re slightly mysterious. I know a lot about your views about men’s style, a topic I care about a lot as well. But I don’t know much about you. I don’t know what you do when you’re not constructing elaborate and carefully researched menswear threads for social media.

Derek Guy
I wish I had an exciting answer for that, but I work all the time to pay for skyrocketing rents and walkable neighbourhoods, which is the other theme on my Twitter account. So I, if you’re wondering what I do outside of writing about menswear, there’s I eat and sleep. That’s not very much I do.

Rob Armstrong
And writing about menswear is your job. You write articles. You’re a menswear journalist in some way.

Derek Guy
I suppose. Yeah.

Rob Armstrong
How did you become interested in fashion originally? Have you ever worked in the industry?

Derek Guy
No, I’ve never really worked in the fashion industry. I’ve only worked as a menswear writer. But I became interested in clothing, I think when I was growing up, if you had an interest in clothing, it was adjacent to another interest, like you were into punk or you were a skater and you dress according to that subcultural identity. So like a lot of people, I was into music. And, you know, I went to clubs and at those clubs a lot of people wore things like Tommy Hilfiger or Nautica, but they wore it in this kind of streetwear way, and the best dressed guys wore Polo Ralph Lauren from head to toe. And I was friends with some guys that were colloquially known as Lowheads, and it’s basically a streetwear version of those classic American brands.

Rob Armstrong
So was it punk music you were listening to in San Francisco?

Derek Guy
Yeah. I had friends that were in the punk scene. I think if you’re into alternative scenes at that time, you know, you probably had friends across alternative lines. But yeah, a lot of guys that were into hip hop at the time wore preppy clothing but wore it in a more streetwear way. And through that interest, just like how hip hop introduced me to soul, R&B, jazz, blues, going through Ralph Lauren introduced me to classic tailoring, workwear and all these other kind of aesthetics.

Rob Armstrong
So you have a million followers on the platform formerly known as Twitter, and I infer from that that there are a lot of men out there who are interested in dressing well. There seems to be a kind of thirst out there for guidance among men. Do you see it that way? And if so, what do you think that’s all about?

Derek Guy
Well, I have to say, I don’t know why anyone follows me. I originally had around 50,000 followers in the end of 2022 or so, and I know why those original 50,000 people followed me. It’s because they’re all fellow menswear nerds. I admit I don’t know why other people follow me. I’m often baffled, but I’m cursed with this like, 90s mentality of don’t sell out and do it for the love. And I mean, it’s just my own weird hangup, but...

Rob Armstrong
And you don’t take money from people who make clothes either.

Derek Guy
I’m happy to take it if they’re advertising on my blog, but I don’t do collaborations. I don’t do paid tweets. But and I know this is gonna sound cheesy, but I have gotten emails from people sometimes. They’ll say, your tweets helped me find a wedding suit, and I just wanted to send you photos of my wedding. And I’ve gotten a few emails from people who have said that your tweets have inspired an interesting clothing in me and that has been very rewarding.

Rob Armstrong
Derek, let me flip my last question on its head. Following you and following the responses to what you say on social media, it’s very clear that there’s a big population of people out there who are infuriated by the idea that clothing is important. The idea that it is possible to dress better or dress worse, that there’s real standards for this kind of thing, however flexible. Why do you think your love and interest and curiosity about clothing pisses a certain slice of the internet off?

Derek Guy
Yeah, there is a certain portion of the population that sees clothing as frivolous, and that’s the prejudice that’s long rooted in western culture. For example, the story of the emperor has no clothes. That’s essentially about a vain man who everyone mocks. Karl Marx, for example, used the word fashions as a pejorative. Many philosophers have always looked down on clothing because they’ve seen it as fleeting, unserious and not substantive. However, I think most people are interested in clothing to some degree because most people are tuned into the semiotics of clothing. So for men, if you give them the choice of wearing pink jeans or blue jeans, they will have a preference based on what they think the jeans telegraph.

Rob Armstrong
When you say semiotics of clothing, say a little more about what you’re talking about there.

Derek Guy
So clothes are not just clothes. We don’t just choose clothes to cover our bodies. The designs and colours and details of clothing also signal something socially. And we know this on a very basic level. As I’ve mentioned earlier, most men have a preference between blue jeans and pink jeans. But if asked to go to a wedding or a funeral, they generally know that they’re supposed to wear a suit. And it’s not that a suit is designed to keep you warm or something. A suit is designed to connote certain things, to signal something when we arrive at a certain place. And I think that’s also true for casual wear. And I think when you understand the semiotics of clothes, how to express yourself through clothing in the way that you would express yourself by writing a sentence, it’s easier to figure out how to wear trucker jackets or leather jackets or parkas or jeans or whatever it may be.

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Rob Armstrong
While we’re on the topic of the semiotics of clothing and the messages we send each other with clothing, I think it’s amazing how over the last 80 years or so, the set of signals and the language has changed. I call this the great casualisation. Sometime around the second world war, end of the second world war, we had a certain set of codes for how men and women in America should dress on a certain set of occasions, and over time, more and more and more of that code has fallen away. It seems like the great casualisation went into hyperspeed in the last 20 years, and then to warp speed in the pandemic. You know, people talk about the tie is dead and so forth. Do you have a view of what has happened to us over those decades and whether we should celebrate or regret what has happened?

Derek Guy
Well, I would reframe it slightly. I would not call it casualisation, but the expression of different identities. So something that I often talk about on Twitter is that the suit was once considered essentially the cargo shorts of its day. And a proper, quote un quote, gentleman in the sociological sense would have never worn a suit because it was considered too casual. As industrial capitalism started to bloom in the early 20th century, late 19th century, the classes saw their fortunes rise. Those were the people that ended up taking on a higher status, essentially merchants, business people and so forth. And then the suit started to take on new meaning.

And then as we move into the 1930s, 40s and the post-war period, what we see is the expressions of different identities. So a man could have gone to Brooks Brothers to get their classic American wardrobe. They could go to Armani to look like an Italian playboy. They could go to Levi’s to dress workwear. And then by the end of the 20th century, you have all of the expressions that we discussed earlier. Punks dressed a certain way, skaters dressed a certain way, hip hop heads dressed a certain way. And the shift, I would say, is more about less casualisation and more opening the space for the expressions of different identities.

Rob Armstrong
So it is something to be celebrated, in short, that we have seen society has become, as it were, less stratified, if that’s the right word. And as a result, there are more expressive possibilities. The palette has only increased.

Derek Guy
Yeah, I meet people who listen to hip hop and they dress like goths. I meet people who look like they step out of Brideshead Revisited. They’re super preppy, but they listen to, like, techno music. Clothing has become increasingly decoupled from identity. You can use clothing to express things that may not even be true about you. And that, I think, is what’s so confusing now at this moment on how to get dressed.

Rob Armstrong
Yeah. There’s a trend in clothing that is run in parallel to the one that we’ve been discussing, but that is separate. You’ve written about this a lot, which is that high-quality clothes seem harder and harder to find. Am I getting that right? Am I just shopping in the wrong places? Has there been a trend towards a lower quality? And how come? Is there not a market for high-quality clothing anymore?

Derek Guy
I would separate this out into womenswear and menswear. I . . . sometimes I watch womenswear content where they discuss quality, and I’m shocked at the kind of cuts to quality that is happening at the womenswear aisle. I don’t think it’s that hard to find clothes that last on the menswear aisle, unless you’re buying things that fit extremely slim, and then at which point seams will be stressed and things will break down. But if you avoid fast fashion and you’re not buying clothes from Shein, Zara, H&M, the thing to pay attention to is what I call emotional durability, which is your relationship to your clothes. Paying attention to how to dress for your body type, how to wear things even if a trend has passed. How to buy things that you’ll love wearing not only on day one, but in year 10. I think that’s a more important measure. Because most clothes will hold up.

Rob Armstrong
Well, let me ask you then one nerd to another, this is a dilemma that I face. I love tailored clothing, but there are fewer and fewer occasions in American life that kind of call for it. And I don’t like being in those situations where you’re just wearing something that you feel comfortable in and that you think looks great, and you walk into the room and people are like, whoa, look who’s wearing a suit. What are you dressed up for? And I’m like, yeah, why did I bother? You know, is there a way to be the kind of nerd that you and I want to be without having to sort of explain yourself all the time?

Derek Guy
Well, there are ways to dress down tailored clothing. One obvious way is instead of wearing suits, wear sport coats. Wear them in rustic materials like tweed and dress them down with things like western denim shirts and jeans instead of tailored trousers and dress shirts.

Rob Armstrong
Sure. Agreed.

Derek Guy
So, learning the language of formality and tailored clothing and learning how to dress things down coherently so that things still look beautiful but dressed down, I think, is one way. The other way is just to have a sense of humour about yourself and know that you know you might be dressed differently than others, and over time people will just be like, oh yeah, that’s the guy that wears tailored clothing, suit . . .

Rob Armstrong
Wears a tie at work. That’s a life lesson right there. You know, if you just stick with your eccentricities, people will accept you. I think that’s beautiful.

Derek Guy
I think if you don’t judge other people for their dress and you have a sense of humour about yourself and you’re not actually pretentious, then a lot of those fears will go away. Because oftentimes when people say, you look really nice today or you know you’re wearing a sport coat, they’re actually paying you a compliment. And if you have a good sense of humour about yourself, it becomes just a fun thing.

Rob Armstrong
OK, just taking the opposite end of the same question, if you want to wear streetwear or casual wear, workwear or anything on that end of the spectrum, but you want to present as pulled together all the same, are there guidelines for that? Is there a way to do that?

Derek Guy
So I would emphasise here that once you leave the world of tailored clothing, not everyone is going to like how you look. It’s like regional dialects. It’s going to be beautiful to some people’s ears and horrible to other people’s ears. But I think a way to express it better rather than worse is to understand the history of the aesthetic and to understand the cultural guidelines and the rules of how to form those looks. It sounds very basic, but I would just go to Instagram and follow people who you think dress well according to the aesthetic. Look up brands that you like, and then go to that brand’s Instagram page and click the tag section and then find people who think look stylish in those clothes and see what are the brands they wear.

And then, you know, if you’re interested in workwear, pick up a book about jeans or watch like 1950s, like, rebel films. Or, you know, if you’re interested in streetwear, read about hip hop and punk and skate movements and watch films that are related to those movements. Paying attention to that kind of like social history and cultural language and following accounts that dress in the aesthetic that you like is probably the best way to develop that sense of style while recognising that your look doesn’t have to be for everyone, as long as it expresses what you want and makes you feel happy.

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Rob Armstrong
Taking on board everything you’ve said about how history and context affects and defines what makes a person dress well, are there items or kinds of items or certain things that every wardrobe needs to have.

Derek Guy
So there is one thing that I think everyone should have, and it is a dark suit because things like weddings, funerals, court appearances, christenings, all of these events usually call for a dark suit, and sometimes they can come up at inopportune times and you don’t have time to get something together within a week. So you should shop for that, like, immediately.

However, the rest of my list tends to be things that I don’t think that there is a list of must-haves for everybody because people have different lifestyles. They come from different backgrounds, regions. There’s just so much kind of openness now in our society, so I would feel more comfortable saying that if you’re starting to build a better wardrobe, there are certain things that will help you develop your own taste. So to me, some of those items include a pair of blue jeans, grey sweatshirt, a Shetland sweater in a basic colour like navy or brown, light blue dress shirts, navy sport coat, grey trousers and a material that suits your weather. So either tropical wool for a warm climate or flannel in a cool climate, and then three pairs of shoes, ideally two leather shoes, one pair of sneakers and then some casual jackets like a field jacket, you know, something like that. Or maybe a Barbour or something.

And the reason why those things are good is because those end up forming a baseline. I mean, those are things that you could ostensibly just wear forever and you’re just done with it, which is fine. But they also can be things that allow you to play with different aesthetics. So you might wear the navy sport coat for a while and then realise I’m not really a navy sport. I’m not really even a tailored clothing guy. Like, this just doesn’t work for me. But now you have a navy sport coat for Mother’s Day, or like going out on date nights or whatever, going to a business meeting, it can still be a useful item. And the tailored trousers that you used to wear with your sport coat can now be something that you use to play with smart casual looks.

Rob Armstrong
Derek, my mother really prefers skatewear.

Derek Guy
But speaking of skate wear, you know, those jeans can be something that you wear with like classic casual wear, like that Barbour jacket. But then you realise you’re not really a classic clothing kind of guy. And those jeans can be worn with a pair of vans slip-ons and like a trucker jacket or something, or even a streetwear jacket. Not to say that every person should dress in a certain way, but these are items that allow you to explore your taste so that you don’t have to reinvent your wardrobe every time your taste takes a different turn.

Rob Armstrong
Great answer. OK, now, as a way to wrap up a little bit, Derek, I’m going to really challenge you with something that is going to be difficult for you because you’ve been uniformly positive in this interview. And you see, as long as people are coherent with what is in their heart and soul and are making choices that resonate with their identity, then you’re well on your way to dressing well. But I want to know what you really hate. I want to hear about clothing items that you absolutely despise. Is there anything you just can’t stand?

Derek Guy
I do make a lot of jokes about it on Twitter, and I hope they’re not . . . before my account started growing, I made a lot of jokes about Allbirds because it was just like an easy joke among guys who were really into clothes. But then over time, I ended up making jokes about dress sneakers, which is my term for this emergent style of shoe that has a dress shoe upper but a sneaker sole.

Rob Armstrong
The worst! I called those in a column — I think it’s coming out this weekend — the worst shoe in the world. The one with that. That’s like light brown with a white sole.

Derek Guy
Sometimes they’re blue, sometimes they’re black and they could be any colour. But I think of it as essentially like wearing a t shirt with a tuxedo print. It just doesn’t make any sense. And I think in any casual outfit, you would look better with just like a pair of classic Nike’s or Adidas or Vans. And then in a tailored outfit, I think you would look better in a pair of . . . it could be anything from like penny loafers to Derbys to Oxfords. It depends on, you know, the tailoring that’s involved, but basically a traditional leather shoe. And to me, a dress sneaker is neither of those things in that it ends up being this like neither fish nor fowl thing and it just looks ugly. So . . . but that said, you know, if someone walked into the room in a pair of dress sneakers, I’m not. I don’t actually really care, you know, what that person wears.

Rob Armstrong
Derek, thanks very much for being on the show.

Derek Guy
Thank you so much for having me on.

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Rob Armstrong
That’s the show. Thank you for listening to Life and Art from FT Weekend. Check out our show notes where there are some links that will get you past the paywall to related pieces on FT.com. We’ve also got ways to stay in touch with us on email and on Instagram. I’m Rob Armstrong and this is our team. Our senior producer is Katya Kumkova. Our producers this week are Lulu Smyth and Julian Weller. Our sound engineers are Breen Turner and Sam Giovinco with original music by Metaphor Music. Topher Forhecz is our executive producer and our global head of audio is Cheryl Brumley. Have a lovely weekend and we’ll find each other again on Monday. Have a lovely week and we’ll find each other again on Friday.