Talking to Derek Guy, the oddly private fashion hobbyist with a million followers, about the vacuity of trends, why it’s hard to find good jeans, and the stratification of luxury and fast fashion.
by Lauren Sherman
Guy blames capitalism, greed, and the downfall of mainstream fashion media as to why the majority of people dress poorly despite fashion’s role in pop culture. Photo: Christian Vierig/Getty ImagesFashion is a bigger part of popular culture than ever, and yet the majority of people dress poorly. Why? Derek Guy, a writer who has become ultra-famous on Twitter over the past two years thanks to his menswear explainer threads under the handle @dieworkwear, has ideas. They have to do with capitalism, greed, and the downfall of mainstream fashion media. And he disseminates them regularly to his 1 million followers.
Earlier this week, amid the men’s shows, I hopped on Skype with Derek—yes, Skype, he only uses Skype—to talk Big Luxury, Elon, skinny jeans, and being nice to people who wear Allbirds. Even if you completely disagree with his position, the ultra-secretive, never-photographed Guy (he swears that’s his real name) will at least help you synthesize your own.
The Man, the Myths…
Lauren Sherman: Do you think of yourself as a cultural anthropologist?
Derek Guy: Cultural anthropologist sounds very haughty.
What would you call yourself?
I’m just a guy who’s interested in clothes. I can’t afford a $10,000 coat. It doesn’t feel relevant to my life. I don’t live in New York City, I don’t go to fashion shows, I don’t hang out with fashion people. I don’t read that many fashion stories because they feel so removed from my life. I would be more interested in reading a story about why pajamas died. I don’t want to seem like one of those guys who says, I don’t watch TV. I don’t like football.
There are many people who wear designer clothes. Why aren’t you interested in why they want those clothes?
It often feels like a trend is happening, and then everyone buys a ton of the trend, and then they say the trend is no longer happening. To me, that just doesn’t feel very interesting. It just seems fake.
Where does your expertise come from? Have you worked in the industry?
I’ve been writing about the industry since 2011, but I’ve never worked for a clothing company. And I don’t know what it means to work in the industry. I’ve used a bunch of bespoke tailors, and that’s where my information about tailoring comes from. I talk to some of the leading dry cleaners, people that manage factories, that’s basically it.
Did you have a job before you started writing?
I like to keep that private.
Why?
I’m just a private person.
Is Derek Guy your real name?
Yes.
When you started writing about clothing around 2011, was that for publications? Or Tumblr?
Yes, Tumblr, blog, forums. I was a hobbyist. I don’t think that it’s really even that unusual.
No, but it is unusual that you’ve made such a career out of it. Eugene Rabkin was the forum. Susie Bubble, who was on theFashionSpot a lot, became a famous influencer. The career you’ve built is pretty singular.
It’s not like Twitter pays me five figures a month—which someone suggested and I thought that was hilarious.
I can’t imagine you get paid much at all from posting on Twitter, but you probably get a lot of jobs because you’re now seen as an expert, right?
After the Twitter thing, I’ve gotten a few more jobs from some mainstream publications, but it hasn’t made a huge impact on my income. I do get some money from Twitter Blue. Mr. Porter pays me to write a monthly column. I turn down a lot of stuff because I don’t want to partner with brands. I have a very limited scope of what I feel comfortable monetizing.
You make income outside of writing?
Yes.
Portnoy’s Complaint
Back to Twitter. I have this image in my head of you, early in the Elon administration, getting called into a room with him. You were active on Twitter before, but your online influence really took off after Elon took charge. What happened?
In the fall of 2022, [Barstool Sports founder] Dave Portnoy came out with a watch company. From 2011 up until that month, I was only really tweeting to enthusiasts, and making in-group jokes about brands like Kapital and Engineered Garments. I thought Portnoy’s watch thing was a huge ripoff. I don’t remember the price, but pieces were somewhere north of $2,000 and I said, I can’t believe that somebody would charge their fans like two Gs for a $40 quartz movement. I wouldn’t even do that to my enemy, because I think it’s so dishonest. Those tweets went viral. And then Dave Portnoy made a video where he complained about me.
It just seems so crazy, that someone with his success would even notice something I said. And then, after that video, I did a thread. In October, I had maybe 50,000 followers. By the end of the year, that probably doubled. Suddenly, it didn’t feel right to make jokes about Kapital and Engineered Garments, or make fun of Allbirds, because now I had a following of people who earnestly like and wear Allbirds. I found that people liked informational threads. I am totally confused by why people enjoy hearing my thoughts. I don’t really have any explanation for it.
I’m not confused by it. I am confused by the Twitter algorithm promoting you so heavily. You have almost 1 million followers. Have you ever been approached by Musk or his team?
Someone emailed me once: I don’t know if I want to say that because, partly because, I don’t want people to know that I have an email address, and I don’t want people emailing me. Let’s just say that sometimes people ask me questions. Once, someone asked me, How do I get a dinner suit? And what do I wear with it? I answered the question. And then the person said, Thank you. I appreciate the advice. A lot of us over at Twitter appreciate your work. Then I looked at the name, and they worked at Twitter on some high level. I don’t know the exact position. I’ve never spoken to Elon Musk.
The Tight Clothes Debate
There are a lot of different types of people who follow you: right wing, left wing, neoconservatives, Allbirds wearers. You are unafraid of engaging politically, using clothing as the context. Have you created certain guardrails around what you’re comfortable discussing?
There are certain things that are important to me, like immigration, and mass shootings. If you love clothes, it’s weird to me if you’re anti-immigrant, because those are the people who make your clothes. If you’re xenophobic, that’s a weird disconnect. I don’t like the question, because I don’t think about what is a kosher post.
Do you think it’s a race to the bottom to make cheap things? A pair of jeans that cost $20 in 1950 might still cost $20 today, so of course the quality has diminished.
Quality is a very nuanced concept. Unless you’re buying Shein, most clothes are fine in terms of wear. Some stuff wears out very quickly because people buy, like, really tight clothes, and they’re putting more strain on those clothes. If you buy looser clothes and you wear them for a long time and you repair them, I don’t think the quality is so bad, at least on the men’s side. If you buy a J.Crew shirt, and you don’t buy it super tight, it will last a long time. To me, the biggest problem with durability nowadays is not the make of the clothes, but the design.
Why do people buy clothes that are too tight? Is it trend-based, or is it because we’re an overweight society and people are trying to squeeze into a smaller size, or both?
In the early 2000s, designers made slim-fit clothes as a reaction to the oversize fits of like, Armani, in the 1990s. Over time, the slim silhouette became popular in mainstream stores, and now every guy squeezes into these really tight clothes.
That’s changing now, right? Everything is moving toward a bigger silhouette.
You have to pay a lot of money. I was talking to somebody who runs a denim company and asked why they don’t introduce a looser fit. If you’re a guy and you’re looking for a looser fit in denim, you have to pay $250 to all these designer brands—$250 and up.
I’m in Oslo right now, and pretty much everyone is dressed badly. [Note: Except for the people at Kafeteria August.] In most big European cities, in Milan and Paris, and even in London, they try. Here, I might as well be in Podunk, U.S.A. The clothes don’t fit. There isn’t a sense of fashion, nothing. Do you think there’s any chance that we can collectively go back to wanting to look nice?
Most people don’t have very much interest in clothes, and the market is confusing. There’s a hollowing out of the middle; there is either fast fashion, crappy clothes, or a $300 pair of jeans—sometimes even a $1,000 pair of jeans, which is insane for most people. Then, there’s just more cultural language to deal with. There are hundreds of aesthetics, and there are no simple guides. You have to figure your way into some TikTok stream or into a Discord, or the right Instagram account.
Stores are worse now, too. There are fewer good stores, fewer skilled sales associates. You go into a store and everyone’s just kind of shoving some crappy thing into your hand.
If you were sitting in a room with a luxury brand—or a fast fashion brand, actually—as a paid consultant, what would you tell them to do?
I don’t have any views on what I think they should do, but I think the fashion media should be better at telling people about clothes and how to choose clothes and stop caring so much about celebrities and trends.
Well, it depends on if you consider yourself a service journalist or a news journalist. It became less important to those publications to do service journalism when you can go on YouTube and find an explanation of how to tie a tie.
I don’t want to sound like a hippie, but these big media organizations and big brands would be better if they were just small operations without huge bills.
What keeps you caring about this stuff?
I’m a hobbyist. Why do people build little, tiny model trains?
I truly don’t know.
