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Ernest Wilkins was looking for a T-shirt. Something specific, the Chicago-based writer and publisher of Office Hours Magazine explained: “I saw this weird Instagram brand pushing Enron merch one day and it got me thinking, there’s probably a real Enron shirt out there for a fraction of the price.” A deep eBay dive for Enron gear didn’t pan out, but it did turn up a money-green Lehman Brothers banker bag that looked perfect to take to the gym. The now-defunct financial firm was once considered too big to fail. But as Wilkins learned, it once produced swag that now seems too good to pass up.

Lately, these slight sartorial nods to the moneyed and powerful of yesteryear are everywhere. It’s not so much about flaunting your wealth as it is taking cues from Masters of the Universe past. It’s a vintage Rolex hat going for over a hundred bucks on Grailed. A shirt touting your membership in the fictional “Hamptons Sports Club.” The Princess Diana-inspired “I’m a Luxury” sweater that you see all over Instagram. This is not the preppy comeback that seems to recur every few years. This is something different: less Take Ivy, more die yuppie scum. But please leave me that dope windbreaker the dealership gave you with the Saab 900 you bought in 1991.

Princess Di-inspired sweaters from Rowing Blazers.

Courtesy of Rowing Blazers

For some people, wearing a vintage red Mount Gay sailing cap is meant to let others know that you are a person that owns a yacht, or perhaps that you’d like to some day own one. For others, it’s a bit of ironic gesturing. You likely weren’t hanging out with the Wolf of Wall Street in 1991, but anybody that’s up on their Marty movies can appreciate a Stratton Oakmont longsleeve. Or maybe you’re obsessed with old Ralph Lauren ads from 20 or 30 years ago, and your whole “waxed and vaxxed” summer vibe is “extra from a movie based off a book from about a group of beautiful people in a love hexagon stuck in an English estate”—and now you can find that stuff vintage for a lower price. Whatever it is, most of us just spent an entire year being as unglamorous and unsexy as possible, and there is something great about at least pretending like you don’t have a care, reality be damned. If you want to rock a second-hand pair of Gucci loafers with some ratty old jeans, an old madras shirt you got from Wooden Sleepers, a Shakespeare in the Park tote you got from Fantasy Explosion, and a vintage hat from a posh tennis club that you couldn’t possibly afford, then by all means, do it. There’s never been a better time to cosplay as an extra in a Whit Stillman film—or Nora Ephron, if that’s more your speed.

Certain symbols have taken on new resonance. Take the seafood tower. In theory, multiple trays of crab legs, oysters and other crustaceans is a nice treat. But in recent decades, the tower has become one of those things the annoying rich dude at the table next to yours orders to show off how much money he has. That was part of the reason the guys behind the Throwing Fits podcast recently offered up a longsleeve tee with a big seafood tower on the back. “Obviously, depending on how sincere you are with it, it could fit somewhere between subversion and irony,” co-creator Lawrence Schlossman says. “[It] speaks to both purely aesthetic and purely sentimental reasons,” co-creator James Harris adds. He notes that the reason you’ll see a 20-something pay 50 bucks for a sweatshirt memorializing a Mattisse exhibit at the Art Institute of Chicago 10 years before they were born is simple. “I’m seeing a lot of vintage art exhibitions and merch really resonate because, obviously, your regular layman or laywoman cannot afford a fucking masterpiece.”

We all have our reasons for our little nods to yuppiedom past. You might have a hat from the Odeon or some defunct Manhattan law firm because you want to rep your city, as Stella Bugbee noted in her New York story on “Zizmorcore,” the ascension of all things New York; or you might just think stuff with tennis racquets looks dope. Whatever your speed, it seems notable that the trend is cropping up as a billionaire holdover from the 1980s leaves the White House and  socialism becomes sexy.

There’s something weirdly familiar about it all. I’m reminded of the yuppie 1980s and early-1990s: the way, towards the end of the George W. Bush presidency, WASP signifiers were turned on their heads. Seeing a guy skateboarding up the street in a yellow Rowing Blazers “FINANCE” hat in 2021 has a similar impact as seeing a rapper or scuzzy indie rock band wearing boat shoes did 12 or 13 years ago: it doesn’t make total sense, but it looks good. Just look at the humble boat shoe.

Vampire Weekend frontman Ezra Koenig in 2008’s finest yuppie fashion.

Mick Hutson

Up until 2008, the boat shoe was usually thought of as “the typical frat boy look or stuffy old look,” as Cristina Faris, a former product director at Sperry, put it. That brand’s Top-Sider shoe used to conjure visions of people named Muffy and Chip singing the praises of William F. Buckley at their Cape Cod weekend house. Faris points to the spring 2008 collab Sperry did with Band of Outsiders as the moment WASP looks began assimilating into hipster style: “It took an iconic silhouette that everyone knew as one pattern and basically one color and flipped it on its head.” Ezra Koenig of Vampire Weekend and Pharrell both were rocking boat shoes, while Kanye was wearing L.L. Bean duck boots. It didn’t feel at all like a celebration of the former Connecticut-born, Yale-education wealthy son of another former Connecticut-born, Yale-education wealthy former president; in fact, it felt like the opposite. After eight years of the country club running the country, it felt like taking a symbol of that rich and privileged world and making it for everybody. 

What we’re seeing today has a similar feel. It doesn’t matter if you come from a poor family, you’re a person of color, were born in another country, or maybe your family wasn’t allowed to join the country club a few decades ago because your last name is Goldberg. Now you can rock an old Range Rover sweatshirt or a piece from Noah’s collab with Barbour and feel like a cool, modern descendent of some titled P.G. Wodehouse character. Ernest Wilkins feels similarly about being a Black guy walking around Chicago with a banker bag.

“I’m guessing the number of people that look like me who possess [a banker bag] is a very small amount. The likelihood someone sees it and assumes I’m a member of the 1% is very low,” he says when I ask whether he thinks he’ll be mistaken for, well, a banker because he’s carrying a bank bag. But for Wilkins, it’s all part of something larger. “I think about all the Black folks who have been keeping Ralph Lauren rich all these decades, including myself. I think about how we always felt like those brands and labels signified we were getting to the money, which is the essential driving force of American culture.” Now, if you take these symbols of power and wealth and turn them into your look, you’re doing something similar to what the Bronx-born Ralph Lauren (née Lifshitz) did by turning symbols of old-money WASPdom into style anybody could wear, or Dapper Dan did when he made his high-end Gucci and Louis Vuitton knockoffs the signature look of the early days of hip-hop.

Of course, style is always in flux; right now you can walk down the street in any trendy neighborhood in Brooklyn, Oakland, Chicago or elsewhere see a creative director of an Italian liquor brand rocking the western look, or a person clutching a MacBook wearing a pair of Carhartt dungarees. It’s fun to dress up outside of our own realities, and wearing a rich dad’s hat is one way to do it. Of course, that doesn’t paper over the reality that people who aren’t rich almost always don’t tend to generally like rich people. The rich are probably going to continue getting richer, and the rest of us are going to continue hating them for that. But it’s still fun to poke great big holes in the myth that just because you’re wealthy means you’re special.

“We’ve seen New York City be taken over by finance bros in suits that are just balling so hard and ordering bottles of the most expensive shit and not even knowing what they’re talking about,” says Harris. “Those finance bros have poisoned the city. If anything, we’re kind of trying to take it back from them. Free my seafood towers.”

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