The Derek Guylander School for Conservatives Who Don't Read Good

Starting this month, I'm going to do two new things. One is that I'll plan on releasing episodes on a more regular schedule, on the first, third, and fourth Thursdays of each month. The other is that the second of those three episodes will be paywalled, and it will be a bit different in content from my usual podcast. It'll be shorter, typically a half hour give or take, and it will be much more topical than I usually like to be. I'll talk to my guest or guests about some current politics and news, and I'll talk about the literary intellectual controversy or trend of the moment, if there's one at hand when we're recording.I won’t be offended if you don't want to pay, but of course will be grateful if you do. And to my stalwart existing paid subscribers who forked over money when I wasn't even paywalling anything, much gratitude. You're on my hall of honors list, which as you know is hanging in the burned out husk of the Friendly's Restaurant on Sumner Ave in Springfield Massachusetts. -Dan

My guest on the podcast today is Derek Guy, who is North America’s premiere men's fashion journalist and critic. This isn’t a highly competitive category—most fashion writing is dumb and corrupt, and most of it is about women’s fashion—but Derek wears the crown exceptionally well. He shows what’s possible in that space, consistently writing thoughtful, substantive essays not just about what’s hip in men’s fashion but what it means culturally, sociologically, politically.

If you’ve heard of Derek, it's almost certainly because for a while he was an accidental celebrity on Twitter. He was just on the platform, doing his well-regarded but relatively obscure men’s fashion thing, slowly building his online presence, when the algorithm took hold of him and made him ubiquitous on the site, dropping him into the feeds of millions of people who had never shown any interest whatsoever in his subject. As the Wall Street Journal reported in 2023:

Of all the changes at Twitter Inc. under Elon Musk so far, this might be the most unexpected: A California-based menswear writer, who weighs in on incorporating western-style wear into your wardrobe, and on his favorite Italian tailors, suddenly seems to be all over the platform.

The Twitter account @dieworkwear, run by Derek Guy, is popping up left and right in users’ timelines—even for those who don’t follow him. The phenomenon has befuddled users—and Mr. Guy himself.

Derek doesn't know why this happened. He didn't have a backroom deal with Elon Musk. It just happened. He became the “men's wear guy on Twitter.”I initially reached out to Derek not to have him on the podcast, but because I was trying to develop a story pitch on men's fashion in the age of Trump, and I wanted to see if I could pick his brain for ideas. It turned out he was already at work on a few different stories on different aspects of that topic, and it occurred to me that I could kill two birds with one podcast episode.

One of the articles we discuss in our conversation hasn’t run yet. The other, his Bloomberg story “The Evolution of the Alpha Male Aesthetic,” goes back into the history of macho male fitness influencer fashion to explain why the new crop of alpha male influencers dresses the way it does. Among the interesting ironies it points out is that the styles we currently think of as manosphere chic—Joe Rogan in his super tight jeans and super tight t-shirts, Andrew Tate stuffed into slim fit suits like a misogynistic sausage—are directly descended from 1990s high-end fashions that were intended as rejections of machisimo. Guy writes:

Early adopters of slim-fit style were fashion-forward urbanites who embraced this European vision of youthful cool. They wore shrunken blazers, used chamomile-infused moisturizers, and could explain the difference between Chelsea boots and jodhpurs. But their aesthetic rattled the mainstream. In search of a label, the media landed on “metrosexual,” a term that, not so subtly, cast suspicion on a man’s gender and sexuality. The metrosexual was someone who took pride in taste and understood why “some women have 47 pairs of black shoes.” What set him apart wasn’t just his grooming habits or aesthetic literacy, but his attitude towards gender performance. As the New York Times wrote in 2003, this new archetype possessed “a carefree attitude toward the inevitable suspicion that a man who dresses well… is gay.”

While slim-fit marched down high-fashion runways, it also crept through indie rock shows, early style blogs, and menswear forums like StyleForum and Superfuture. These communities turned fit into a kind of doctrine, elevating silhouettes like APC New Standards and Uniqlo button-downs as markers of elite taste. As The Strokes played onstage in threadbare tees and skin-tight denim, wealthy urbanites chased the look by purchasing Slimane's most popular creations: Dior’s 17 cm and 19 cm jeans, named after the width of their leg openings. Those priced out of luxury labels raided the women’s aisle for tight denim, a gender-bending hack that Levi’s would later celebrate with their 2011 “Ex-Girlfriend Jeans” for men. Even the heritage revival got a trim. The traditional symbols of masculinity—workwear, Ivy tailoring, military surplus—were recut for a different era, one where style was no longer bulky but compressed, tailored close to the bone.

In its early years, slim fit was met with derision and low-grade cultural panic. Critics said consumerism had hollowed out traditional manhood, replacing it with men who spent too much time curating their appearance. Others fretted that the rise of shrunken silhouettes was a symptom of masculine decay. But soon, everyone became metrosexual. Fashion magazines treated slim fit as a kind of pseudo-science: shoulder seams had to sit on the edge of the shoulder bone; trousers must taper just-so; any loose fabric signaled laziness or sloppiness. J.Crew helped bring this new silhouette into everyday offices. Their Liquor Store concept shop, opened in 2008, transformed an after-hours watering hole into a menswear-only boutique laden with 1960s-era references to traditional masculinity—antique rugs, leather club chairs, and Hemmingway novels sitting alongside Red Wings—even as they sold slim chambray shirts and cropped blazers. At the same time, Mad Men introduced a new masculine figure: Don Draper. Emotionally sealed off and impeccably dressed, Draper gave the slim-cut suit an edge of stoic authority. Slim tailoring had became synonymous with professional competence and upward mobility.

Eventually, slim fit stopped feeling radical. Its early ties to gender rebellion faded as the silhouette was absorbed into more conventional ideas of masculinity. What once looked subversive—shrunken jeans, tight shirts, tailoring that clung instead of concealing—became standard fare in offices, weddings, and Tinder profiles. New subcultures rebranded the look with more conventionally masculine associations. EDC (Everyday Carry) enthusiasts, armed with pocket knives, flashlights, and multitools, adopted slim-fit gear as part of a rugged preparedness ethos. Their slim tactical pants and fitted henleys weren’t about gender ambiguity; they were survivalist uniforms. Athleisure brands such as Rhone and Alo Yoga pushed the same silhouette in poly-stretch fabrics, merging gymwear with streetwear into a softer kind of masculine armor. In Silicon Valley, tech founders embraced minimalist wardrobes built around Everlane tees, slim joggers, and all-white sneakers. The aesthetic once dismissed as “metro” was now treated as self-optimization. Slim fit, in the end, didn’t rewrite the code of masculinity. It just offered a new way to perform it.

In addition to the two stories we discuss, he's also gone on to write a new story on a person we discuss in the conversation - Trumpist intellectual Michael Anton, who is a huge clothes horse and for a long time was a regular presence on high end men's fashion forums. It's a fun conversation, particularly if you're interested in questions of masculinity, culture, and identity. Listen!

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