@Dieworkwear, Twitter’s ‘Menswear Guy,’ Is Just as Perplexed as You Are

Are you being stalked by tweets about how to avoid fast fashion in menswear? The best way to shrink an oversized vintage sweater? Where to buy sick, affordable Etsy outerwear? Deep thoughts about impeccable tailoring? 

You’re not alone. Ever since Twitter rolled out their algorithmic “For You” tab, one man rules your feeds. You know him by his bespectacled avatar, his prolific threads about menswear minutiae, and his Aimé Leon Dore jokes. He’s the man they’ve started calling: “Menswear Guy.” 

But who is he, and why is he suddenly everywhere?

“My guess is as good as anybody else's,” Derek Guy, the California-based founder of @dieworkwear, told me in a phone call on Wednesday night. (That’s his real name, but he keeps his age and most everything else private.) 

“I think I get more engagement in my feeds. I get more people asking questions. Even if you don't follow me, if a bunch of people around you follow me, then I will pop up in your thread. Then Twitter thinks that, ‘If a bunch of your friends like it, then you might also like it,’” he said. “That's what I assume.” 

Either way, Guy is just as perplexed as you are: “The only thing I think that made me feel self-conscious is I literally went out to lunch with a friend today, and he said, ‘You are like every third thing on my timeline.’” 

On one hand, he’s glad to have new, curious followers who are interested in clothes. On the other: “If someone asks me a question like, ‘Where can I get a suit?,’ I've been like, ‘Can I reply to this person without 10,000 people seeing it?’ I don't want to be every third thing on someone's timeline. That's got to be annoying. I hope if someone really doesn't have any interest in it, and if I really bother them, I wouldn't mind if you blocked or muted me.” 

Guy’s initial interest in clothing as self-expression began in high school. He was friends with musicians who were Lo Heads, or vintage Ralph Lauren collectors. “I admired people who dressed really well and felt like I was somewhat cognizant of how people use clothes to project an identity or create a persona,” he said. A few years after that, he became invested in tailoring when a friend he had feelings for asked him to accompany her to a wedding, and he wanted to impress her. “Starting around the early 2000s, I just got really interested in suits because I had attended weddings, and I was watching old French cinema and listening to a bunch of jazz,” Guy explained.

He then got immersed in reading menswear blogs and forums in the mid-aughts, back when The Sartorialist ruled the streets and nobody could shut up about sprezzatura. By 2010, he started a blog called Die, Workwear!—an inside joke and light jab about a friend who wore a ton of workwear. “The heritage movement was so big and everyone was dressing like a lumberjack and barber and plaids and all this stuff,” he said. (Were we ever so young?) The Tumblr led to him getting other menswear writing gigs, and he still maintains a site by the same name, though it tends to be more philosophical instead of service-oriented—the latter is what Twitter is for. 

Though Guy has been on the platform since 2011, since gaining new normie followers who aren’t necessarily menswear-heads, he’s revived more direct advice, such as a recent thread on how to dress for larger male figures. “For guys who have been paying attention to menswear for a long time, a lot of the information there's super basic,” he said. “It has been nice to be able to share things that sometimes I feel is too basic and I'm afraid to say. Sometimes you say it, and then it turns out some people may not know that, and then they may find the information useful.” 

He was hanging out at around 25,000 followers for a while until November of last year, when two things happened. The first was a beef with Barstool Sports founder Dave Portnoy. Portnoy had just launched a watch line called Brick Watch Company, and Guy pointed out that the watches were retailing for $2,400, but had $40 movements. In response, Portnoy made a video calling him out directly.  

“He starts off with this rant about how much he hates me, essentially. Which made my day,” Guy said. “I still think that the watch is a ripoff, but I don't think that he's intentionally scamming people. I just think he went into it not knowing what he's doing. Even without my comments, a lot of the Barstool guys hated the watch.” 

His comments on the watches led to someone posing the same question about, say, a cashmere sweater sold at a markup by a luxury brand. So, in response, Guy posted a long, informative thread breaking down the ins and outs of cashmere production. He ended up gaining another 25,000 followers over the course of that, and now has over 110,000. 

With a great follower count comes great responsibility, of course. Guy has found himself reining in some of his more insidery jokes—“I don't want to tweet a niche joke about Engineered Garments or some brand that no one's heard of because it's not going to land”—as well as letting up on some of his favorite targets. “I also feel weird making jokes about Allbirds, which was a running joke for me in the past,” he said. “I thought it was a harmless target because most guys reading me are not wearing Allbirds. But as my audience has grown, I would never want someone to actually feel bad about their clothing choices.” 

The one lesson he hopes people take away from his omnipresent feed? 

“Something that I tried to communicate in my tweet threads is that I think clothing and style and fashion is the language. And just in the world, there are many different types of languages and they are all governed by different ‘rules,’ and even within that language, people can break rules and still communicate beautiful things,” he said. “I think that's true of menswear. Instead of trying to dictate to men how to dress, I try to hopefully instill in them that there's a language in dress.”