After the presidential election, many fashion and lifestyle influencers began to come out of the closet as conservatives. Some, like tradwife TikTok darling Nara Smith, were predictable, while others were less so. But what was clear was that MAGA culture, and the fashion and aesthetics associated with it, were becoming increasingly mainstream.
Inauguration weekend, with its mix of parties and formal events, brought together the who’s who of right-wing players. Observing the proceedings was Derek Guy, known online as @dieworkwear—a longtime menswear enthusiast and writer who has came to prominence as an influencer on X for his hot and unnervingly well-informed takes on the sartorial choices of everyone from Donald Trump to Andrew Tate, and what they might be telling us about this political moment.
WIRED spoke with Guy after Monday’s inauguration ceremony to get his takes on MAGA fashion, what it says about who the party is for, and what the richest men alive are wearing these days.
This interview has been edited for clarity and length.
WIRED: First, give us the reviews of the inauguration suits and ties. What are we looking at here? These are some of the richest men in the world, but I’m not sure they really look like it.
Derek Guy: You can break up the inauguration almost by age. The older someone is, the more likely they are at least avoiding the worst of what we’re seeing. And the younger someone is, the more likely they are wearing something that looks cheap, because tailoring as a craft has mostly died in this country. Many people shop ready-to-wear. And when you’re very wealthy, you are probably just buying a luxury-level off-the-rack suit. And just because something is made with fine materials doesn’t necessarily mean it fits. So you have a market system that makes it difficult to find a good suit.
If you’re younger, like Mark Zuckerberg’s age, you’re more likely to kind of fall into this short-jacket silhouette that you think looks modern and hip but frankly looks really dated and makes you actually look more middle-aged, like someone who learned how to dress in the early 2000s.
Vivek [Ramaswamy], for example, wears really shrunken suits. Jeff Bezos often wears pretty good tailoring but today wore a very short jacket which did not look very good on him. He looked surprisingly bad today, given how he looks in tailored clothing other times.
Elon Musk, I’m pretty sure he wears a Tom Ford suit, because that’s five buttons on the cuffs. I thought it looked pretty good on him, but he looked bad at the rally last night. He was wearing a short overcoat with gray jeans, and it didn’t flatter him very well. The outfit didn’t make much sense.
Zuckerberg, his suits are neither fantastic nor horrible. Tim Cook and Sundar Pichai, they are still clearly nerds who don’t care about clothes.
But, you know, for example, JD Vance has a custom tailor. He has a 90-year-old Italian tailor in Ohio. That guy is not following fashion trends.
Why do the rank-and-file MAGA enthusiasts favor such slim-fit suits when Trump himself often wears things that are quite baggy?
What you’re seeing is young conservatives will often wear very shrunken suits because they care more about the tailored aesthetic. Ironically, you actually look better if you’re the kind of young Democrat who doesn’t care about aesthetics at all. So then you wear a sloppy suit. You still look bad, but you essentially avoid the shrunken look. The MAGA aesthetic will change over time as conservatives change their tastes naturally. But I mean, just to be frank about it, many conservatives are often behind on fashion trends.
We are at this moment where the large part of the market has shifted away from the shrunken look of the early 2000s. But if you’re kind of behind on fashion trends, you still think that looks good.
Are you seeing changes to the hallmarks of the MAGA aesthetic, particularly as we’re seeing it merge a bit with the quiet luxury vibe that became very popular online?
MAGA is a very populist aesthetic, so it’s intentionally vulgar and thumbing its nose at WASP morality and aesthetics, even though within the Republican Party there is still that kind of celebration of bourgeois 1950s aesthetics.
I often like to contrast it. When Ronald Reagan and George Bush were first inaugurated in 1980, the Republican Party commissioned custom blazer buttons commemorating their inauguration, and they gave them out for free to attendees at the various events surrounding the inauguration. So if you attended Reagan’s inauguration in 1980, you would have gotten a brass button commemorating the inauguration, made by Ben Silver in Charleston, South Carolina. It was presumed that people who attended Reagan’s inauguration would have a navy tailored jacket. And if you put brass buttons on a navy jacket then that jacket becomes a blazer. It was presumed that not only would young Republicans have a navy jacket, but that they would want to wear a blazer with a button commemorating Reagan’s victory.
The merchandise surrounding Trump’s movement is gold sneakers and Never Surrender T-shirts and, of course, the red MAGA hat.
To me, this demonstrates the schism between the classic Republican—which is the Brooks Brothers, free-trade, globalist, Reaganite Republican—and the new Republican, which is populist. They pay reverence to Reagan, but they don’t share his politics.
The aesthetic is very much not the classic WASP aesthetic, which used to be the Republican aesthetic. Trump’s own aesthetic comes from the 1980s—the “greed is good” of Wall Street boom times. He wears very padded shoulders and a power tie. He used to wear a banker collar, but no longer. And that’s very different from the demure look of Brooks Brothers WASP. MAGA is a very aggressive, populist “fuck you” to the establishment aesthetic.
When you think about the MAGA aesthetic, are there particular brands or influencers who come to mind for you?
It’s all very campaign merch, and the most mainstream item is just the MAGA hat. It still seems very much like campaign merch. I don’t think there’s anyone else that sets the tone except for Trump. There are certain people that embody that look very well. Forgiato Blow, he has that kind of very loud aesthetic. There was a moment where Viper sunglasses were very popular, which was, I think, driven by Baked Alaska. So there are microtrends in that universe. But it’s really Trump—whatever he releases next, people will wear.
Do you think that sort of classic American look—the Ralph Lauren, the oxford shirt—is that going to be sort of the purview of MAGA forever, or do you see that changing?
I don’t think the classic American aesthetic is strictly MAGA, though. I think a Brooks Brothers look is like the ABC of menswear; that’s like a very classic American tailored look. In the postwar period, right after the end of the Second World War, there was a culture clash between establishment lifestyle–the man in a gray flannel suit who works in a corporate job and has a conventional kind of nuclear family and white-picket-fence house—and the counterculture. That was this kind of liberal side of the political spectrum. They wore work wear and chambray shirts, hippie gear, motorcycle jackets. That all became counterculture.
But if you go back further than that, everyone wore tailored clothing, from criminals to CEOs to liberals and Republicans. Ralph Lauren could not have built his empire if button-down shirts and penny loafers were exclusively conservative attire.
I think it’s interesting that the current status of Republican politics is trying to unite the Brooks Brothers aesthetic with the gold sneakers. Do you see them coming together?
I think that’s the weird dichotomy at the moment, because the MAGA movement and Republicans in general have always been kind of looking back toward some idea of America. Even though not every man wore a suit in the 1950s, the suit has historically been associated with the kind of bourgeois lifestyle. And a lot of conservatism in general is about upholding bourgeois lifestyles, morality, identity, politics, and so forth.
There is now a populist section of the Republican Party that’s not about Reaganism or Bush. It’s very about Trump. And its aesthetic is very different from what William Buckley would have worn. William Buckley would not have worn gold sneakers.
I think they are distinct and contradictory, but people can hold contradictory ideas in their head. We are in an age where politics is very tribal. And so long as it fits the narrative of our tribe, then I think it’s coherent for that group. For Republicans, I think those two very contradictory aesthetics are just now within the party.
The men of tech are new to the MAGA crowd, but many people have noted a significant change in their looks, particularly Mark Zuckerberg’s. Can you talk about what they’re trying to signal and to whom?
I heard through the grapevine within my industry that [Elon Musk] used to have a stylist. I don’t think he has a stylist anymore. Mark Zuckerberg denies having a stylist, but I don’t believe him. He is certainly going through a style transformation in the last year and three months, I would say. Jeff Bezos most obviously has a stylist. I don’t think what they’re doing has anything to do with politics. I think Jeff Bezos went through a style makeover after his divorce. And I suspect Mark Zuckerberg just got tired of dressing like a college student. Elon has clearly given up on his stylist and doesn’t dress very well.
[Zuckerberg] dresses more like an MMA guy. He is wearing the boxy tees and the gold chain. But he looks like someone who updated his look to be trendier. There are a lot of guys wearing that kind of silhouette and gold chain, and I don’t know that that says anything about their politics.
We saw a lot of the sort of “spaghetti Western” vibe happening. What’s your take on that?
As a fashion trend, the Western look really leans more liberal, right now, because it’s popular in big cities. Conservatives now dress like metrosexuals in the early 2000s, and liberals dress like Bush-era conservatives. Conservatives are in slim-tight suits or slim-fit suits, and then liberals are like Carhartt double-knees, Western shirts, cowboy boots. There is some of this inherently on the right because it’s a Midwestern look.
But Elon Musk does wear cowboy boots pretty frequently, as does Jeff Bezos.