No one has told Derek Guy why he appears on someone’s X, formerly Twitter.
“Now that there's only like five people left in the company, I've thought about maybe just asking them directly because I'd love to know,” Guy said.
Guy’s Twitter account, @dieworkwear, helped make him something of a pseudo-internet celebrity earlier this year after the site launched the “For You” feed as a part of Elon Musk's Twitter make over.
Guy was first introduced to the wider internet after a spat between Guy and Barstool Sports founder Dave Portnoy over the latter’s Brick Watch Company. Guy noted that the watches Brick were selling had a $40 movement in them. Portnoy responded with a video calling him out directly.
Guy then posted a thread on how to purchase a quality cashmere sweater which brought in an audience that hadn’t considered clothes carefully before.
When Guy began writing for his own website Die Workwear and later Put This On an audience of people who were interested in menswear came to him, Twitter changed that.
“You don't even have to have an interest in men's clothing. Twitter will put my tweet on your timeline without you even asking, which is a very weird way to find content on this point,” Guy said.
The internet platform also gave Guy access to a mainstream audience off of X, including an advice column for politicians at Politico.
Before his launch into the Twitter mainstream, Guy’s audience were menswear obsessives who understood jokes at the expense of Allbirds shoes. With a wider audience that is not knowledgeable about menswear, the jokes didn’t land.
“I’d wake up every day and there’d be at least one in group joke about workwear or whatever,” Guy said. “I rarely do that anymore because the context isn’t there.”
In the vacuum of context Guy, who is not white, has had assumptions placed on him that included accusations of white supremacy.
“I found that, when I started to make that transition towards tweeting a little bit more about classic tailoring, I got a lot of people imposing their own context on what I'm writing,” Guy shared.
That’s not to say that Guy finds no value in the Twitter conversation. The threads he posts providing technical knowledge and shopping advice moves people beyond a practical relationship with clothes.
Earlier this year, Guy received what he described as, “the best email ever,” from a Twitter user who visited New York City and shopped at the stores Guy recommended.
“Someone has found an interest and love for clothing and they're not just trying to like, get by and as an author, the love of hobby, just love and passion, that’s great,” Guy said.
When Guy first became interested in menswear, he found in the blog and Tumblr pages dedicated to menswear the context that social media can strip away.
On forums like StyleForum and Ask Andy About Clothes, menswear aficionados compiled threads of images that showed clothes either how they were worn or how users were wearing them at the time.
“The Internet has changed, the ecosystems in these communities have totally changed,” Guy said. “It's actually shaped how people understand and interact with the semiotics of discourse.”
When Guy is writing for himself on his site, his work is decidedly focused on the connotations of aesthetic.
“There is a joke online that when I go to look up a recipe and person, it's like for four pages about their grandma. But that's the stuff that I want to write. But I don't want to just give the recipe because I don't care that much anymore.”
For Guy the “grandma” story he prefers to write about centers around the culture that imbues the clothes with meaning. Whether it’s the Shaker community’s influence on knitwear or patrician influence of the once-great American clothier Brooks Brothers, in longform Guy can meditate on the confluence of class, power and symbols.
"When you put on an oxford cloth button down, hopefully you're not just thinking of the middle manager. You're thinking of Miles Davis and thinking of Paul Newman, all the exciting parts of that symbology," Guy shared.
He credits his penchant for cultural writing to the influence of author G. Bruce Boyer. Boyer has been a fashion editor for Town and Country and has written multiple books on menswear. The one that Guy points to is Boyer's 2015 entry "True Style".
“It doesn't pander to saying: how to buy a shirt or how to buy a suit. It's telling this whole story about scarves and other clothes,” Guy said. “I think that's like the best way to write about clothing, it’s the most honest way.”
Boyer, whose books include "Elegance", "Rebel Style" and his latest "Riffs: Random Reflections on Jazz, Blues, and Early Rock", returns the praise.
"I noticed that in his articles, he very often quotes very legitimate sociological sources, and very legitimate historical sources and so forth. Something that you wouldn't expect just some guy on the street to know," Boyer said.
The two maintain an email correspondence but have never met in person, though the earnest nature of Guy's love of clothing shines through.
"I discerned right away that he was a guy who really liked clothes, and he bought clothes, and he, he loved to wear them, and so forth. It wasn't a theoretical concern of his it was, it was a real practical concern," Boyer shared.
After realizing the breadth of his platform when someone he replied to bore the brunt of his following, Guy has kept his outfit criticisms aimed at those already in the public square, including other social media figures and politicians.
“I can criticize your taste in music or food. I can say that have kind of a shitty taste in music. Or a really basic taste in films or whatever,” Guy said. “But, if I say your clothes are ugly, that's very different from me saying your taste in other areas of culture bad because your clothes so close to your skin, they're like an extension of you. It's almost like saying your face is ugly.
Guy intends to stand against the winds of change as the platform that brought him to the mainstream is inundated with them.
"I think [Musk] wants to make it something like an everything app, there's going to be banking, and he just recently launched the live video thing. I don't plan on doing any of that stuff," Guy said.
"I've always just been kind of see myself as kind of a menswear enthusiast I mean, I'm just a guy who really loves men's clothing. I don't have a business plan for my Twitter. I just tweet."
