Finding Your Style: Derek Guy on the Essentials

Title: Finding Your Style: Derek Guy on the Essentials [MUSIC - Marden Hill: Hijack]

Brian Lehrer: Brian Lehrer on WNYC. Now we'll wrap up our Membership Drive miniseries on finding your personal style. Today we get practical. Our guest is Derek Guy, the writer behind the blog Die, Workwear! — or is it Die, Workwear!? I'll ask him in a second — which is also his handle on Twitter and Bluesky, and he's a contributor to the clothing-oriented site Put This On. He's known for breaking down why some outfits work and others don't, often focusing less on trends or brands and more on proportion, construction, drape, things like that. In our last few minutes today, we'll get some wisdom from him about how do you build a wardrobe that works in real life, especially on a budget.

Hey, Derek. Thanks for doing this with us. Welcome to WNYC.

Derek Guy: Thank you so much for having me on.

Brian Lehrer: Did I say the name of your blog with the right feeling? Should I be saying Die, Workwear!?

Derek Guy: Yes. I suppose both is fine. I started that blog many, many years ago and came up with a ridiculous name that makes no sense, and now I'm stuck with it.

Brian Lehrer: That's about men's clothing in particular, right?

Derek Guy: Yes.

Brian Lehrer: In many of your posts, we see that you emphasize proportion, like I said in the intro. That's like trouser rise, jacket length, shoulder width, more than brands and things like that. What should people be looking for visually when they try something on that maybe not every guy thinks to look for?

Derek Guy: Well, the short and long of it is that I think of fashion as a kind of social language. I don't think there is one way to dress, and I don't think there's only one way for pants to fit or whatnot. I think if you start with the premise that dress is a type of social language, and there are many different types of languages today, each shaped by history, just as we're conversing right now in English in a structured manner so that we can communicate with each other, every aesthetic is going to have its own rules that govern its kind of aesthetic.

I think when you're out shopping, it helps first to figure out what kind of aesthetic are you going for in terms of cultural aesthetic. Are you into preppy clothes? Are you into workwear punk, avant-garde? Are you inspired by the way artists have dressed in the past, musicians, academics, these kind of archetypes? I think when you have that goal in mind and you have a certain aesthetic that you're drawn to, use that as a guide to figure out how things should fit, how to combine colors, what's the role of textures in that look, so on and so forth.

I think when guys are just starting to shop for things they want to know, okay, these are the five things to look for, but it's actually-- how suit trousers should fit is not the same as how jeans should fit. How jeans should fit may vary depending if you want a very rugged kind of workwear look, if you like 1980s and '90s hip hop, if you like prep. All of these aesthetics are going to have different ideas of how jeans should look.

Brian Lehrer: You've written about how popular cuts like very slim fits, which could be one of those jeans approaches, or very low-rise trousers, can throw off proportion. What's an example of that?

Derek Guy: We're in this moment where in the early 2000s, slim-fit was all the rage because everyone wore baggy clothes in the '90s. Now that everyone wears slim-fit clothes, looser cuts are coming back into fashion. I would encourage people to just completely detach from that kind of conversation. I just don't think it's a useful conversation. Instead, think of, again, in terms of how you want to dress. If you look at old photos of Lou Reed, he wore skinny low-rise jeans with boots and bomber jackets, chambray shirts.

I was just looking at an old issue-- I think it was published in the 1960s. There's an old issue of Life magazine where they profiled some youths in Southern California. Those guys were wearing these really skinny, cropped, low-rise pants with a Harrington jacket, and it had this kind of mod style to it. I think that looks great. But if you are combining skinny pants, whether it's jeans or chinos or something a little more tailored, you're combining it with an Oxford cloth button-down that's also slim, and you're wearing a quarter-zip sweater, that does have a social language to it. It's often the way many middle-class, middle-aged guys dress today, but it's not a particularly aspirational way to dress, I don't think

Find identities that resonate with you and figure out what are the cuts that go with that. If you want to do a more business casual look, I think if you get a slightly fuller cut pair of pants and a button-up shirt and a textured Shetland sweater, that at least grounds it in something that's a little bit more appealing than the slim-fit business casual that we see today.

Brian Lehrer: What you were saying about slim then baggy, then slim then baggy being in, is it like whatever somebody's parents wore makes you want to gag, but whatever your grandparents wore make you think, "Oh, that's kind of cool"?

Derek Guy: Yes. It's one of the essential dynamics in fashion, as written about by Georg Simmel in the 1902 essay on fashion, as observed by Pierre Bordeaux in his book Distinction. It's that people often dress in a way to signal that they are affiliated with a group, but also individuals within that group. That kind of taste often changes. When I was getting into fashion in the early 2000s, people were wearing slim-fit because it signaled a youthful Euro cool. That was supposed to be opposed to the fuddiness of middle-aged American manager. That has completely changed now. Middle-aged American managers wear slim-fit, so that's why younger people gravitate [crosstalk].

Brian Lehrer: Yes. There you go. Give me one more specific tip here. If someone's building a wardrobe on a limited budget, where might you say spending a little more money actually matters as opposed to where it's okay to save?

Derek Guy: There are certain things-- I would say that I think everyone needs a suit because we all have to go to occasions like funerals and weddings and whatnot. Those things are worn very, very infrequently and probably shouldn't be what you concentrate on if you're on a limited wardrobe. That said, I think you can usually get pretty good jeans and casual shirts for pretty cheap, like pure cotton flannel button-up chambray shirts. Buy used jeans for pretty cheap. They come in so many different cuts now. It's fairly easy to find something on the second-hand market.

I would say where your money goes a little bit further is shoes. It's, in my opinion, a little bit better if you can splurge on a pair of shoes made from full-grain leather rather than corrected grain because they'll look better with age. It's also better to spend a little bit more, if you can, on knitwear because cheaper knitwear will be made from shorter fibers, which will be prone to breakage and then pilling, and they're also prone to stretching out. Also, if you can, splurge on a really nice piece of outerwear because often if you're wearing, let's say, a Champion sweatshirt and just normal pair of Gap or even Levi's jeans or something, you can look really good with, let's say, a really nice raglan sleeve overcoat.

Spending more on outerwear, knitwear, and I think shoes are usually a bigger bang for your buck than going all out for some real expensive button-up shirt.

Brian Lehrer: Hey, before you go in like 30 seconds, if you can do it, and I guess relating to the idea that your parents are uncool but your grandparents are cool. You use a photo of Elliot Richardson, who served as US Attorney General under Presidents Nixon and Ford, as your avatar on social media and the Die, Workwear! blog, I see. Why Elliot Richardson?

Derek Guy: I really admire his style. I have a penchant for classic American style. In the '70s, he wore this long-point collar that was not particularly part of that classic Ivy Style look. He wore a soft shoulder suit and sport coat, hook vent, dartless front, these really tasteful ties. I think if you have a particular fondness for the beautiful history of classic American style, which involves all of these multicultural groups coming together to form something, Elliot Richardson just wore that aesthetic really well.

Brian Lehrer: I thought it was because he resisted the autocratic takeover of Richard Nixon.

Derek Guy: He created something much more superficial.

Brian Lehrer: Derek Guy, the writer behind the blog Die, Workwear!, which is also his handle on Twitter and Bluesky, and a longtime contributor to Put this On. You might know him as the menswear guy online. Derek, this was fun. Thanks for some time today.

Derek Guy: Thank you so much for having me on.

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