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.
Up until 2008, the boat shoe was usually thought of as “the typical frat boy look or stuffy old look,” as Cristina Fairs, 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. Fairs 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.”