Acting like a crook is never in style. But these days, dressing like one is — at least according to the cool kids on the internet.
Like most trends, “preppy” has made its umpteenth return into the fashion zeitgeist, this time tailored to Gen Zers obsessed with ‘90s nostalgia and impersonating Cher Horowitz from Clueless. Scroll through Instagram or TikTok and you’ll notice no shortage of plaid blazers, pleated skirts and cream-colored cardigans draped loosely over shoulders. Take a closer look, though, and you’ll see a deeper subgenre filled with T-shirts emblazoned with the Enron logo or cheeky dad hats with words like “Montauk” or “finance” on the front. The late 20th-century prep aesthetic is no doubt alive and well, but this time around it’s arrived with an overtly satirical take on old-money WASP culture and the corrupt ways in which this culture is fueled, representing a new, darker commentary of the world today.
To understand why Gen Zers are dressing like the wealthy jerk who lives in the McMansion next door, Justina Sharp, a 22-year-old Los Angeles-based creative strategist, points to The Wolf of Wall Street, the 2013 film starring Leonardo DiCaprio, which tells the true story of a slick, money-hungry stockbroker who ran his fraudulent firm into the ground.
“Jordan Belfort is the worst person,” she says. “We all watched that movie. We acknowledge he’s terrible. But to this day, people are making TikToks out of it being like, ‘I want to live like Jordan Belfort.”
Today’s world is a far cry from the heyday of the “greed is good” ’80s, with its skyrocketing unemployment rates and a worsening pandemic that continues to wreak havoc on people’s livelihoods. But when the world feels out of control, fashion is something that can give us back some of that autonomy. Remember: when Belfort’s life was unraveling, he never lost his sense of good taste, continuing to party on yachts, crash fancy cars and spend money he didn’t have right up until the day his world came crumbling down and he was indicted on felony fraud charges.
Belfort’s attitude is the 2020 version of being “a rich, white dad who goes to the golf course and has all the money in the world to spend money on all the stupid things you’ve now decided you need because we’re in quarantine, like a cold-brew press,” says Sharp, laughing.
Thanks to vintage shops, secondhand stores, and brands like Urban Outfitters and Princess Polly, achieving the “casual luxury” aesthetic is easier than ever before. You don’t have to live in New York or L.A. to emulate a glamorous lifestyle — you can be a teenage girl in suburban Nebraska who orders a tennis skirt online and then heads to her high school’s courts with a borrowed racket to take a photo. With the help of TikTok and Instagram, you’ll know exactly how to put your outfit together to make it complete.
“Just like that, you are living that ‘luxury’ and acquiring a piece of that power,” says Sharp. “That’s what outfits are.”
Using TikTok as their tool, Gen Z has dominated the discourse when it comes to fashion by expertly using humor to speak to the problems they’ve inherited. Yes, wearing an “Enron 1997 summer internship” shirt is ironic, but it also speaks to the current cultural climate.
“The fact that we have gotten to this point now where we’re like, yes, we’re all gonna dress up as fake-rich while actively knowing that like most of us can barely afford groceries,” says Sharp. “College is online and we still can’t afford it.”
If that feels more dark than funny, it’s just because it’s true.
“We moved past the point where millennials were doing things that were ironic [to be funny],” says Sharp. “For Gen Z, it’s like, ‘Wow, this sucks. Our planet is burning. Everything’s horrible.’ It’s the fashion equivalent of Pete Davidson making 9/11 jokes constantly. It’s this terrible, depressing thing, but objectively, his jokes are funny and he’s the only one who can make them.”
When it comes to co-opting this finance-inspired aesthetic from the past, Jack Carlson, founder of Rowing Blazers, agrees that there’s a level of self-awareness involved that makes it effective. The kids who are wearing Enron shirts “are under no illusions that it’s going to make their friends think they work at Enron.” This kind of self-awareness, he believes, directly influences how people decide to dress.
“People get dressed to show off knowledge in a way,” he says. “It’s a phenomenon that has its roots in streetwear where what you’re wearing is all about a flex. It’s very different from a traditional definition of luxury where you’re wearing things that show off and the showing off comes in a form of a really expensive fabric or it’s made from a traditional luxury brand.”
Carlson compares wearing an Enron shirt to copping a rare vintage soccer jersey that’s particularly desirable. “You’re not interested in soccer at all, but you’re wearing it to show off that you’ve done a little bit of your homework,” he says. “You have a little bit of knowledge and awareness that this is the coolest thing to have and there can be a little bit of irony to that, too.”
And Gen Z does their homework. With TikTok being used as a vehicle for activism — whether it’s talking about social justice issues like Black Lives Matter or dragging Republicans with satirical accounts — Sharp says she could easily imagine a teen on TikTok not just wearing Enron merch in a video, but taking the dialogue a step further by saying, “Let me educate you on why Enron happened and why corporation XYZ is about to, too.”
For Rowing Blazers, whose website states, “We can’t stand pretentiousness, but we do love being authentic and genuine,” irony is a defining factor of their brand.
“Everything we do is a little bit irreverent and a little bit tongue-in-cheek,” says Carlson, citing the company’s “banker bags” as an example.
“The interesting thing about dressing with irony is that it almost lets somebody take the power back,” he continues. “You can have people kind of appropriating the aesthetic of the world of finance in a way that maybe people wouldn’t view negatively or people would view humorously or kind of empowering.”
As both Sharp and Carlson note, personal style can be empowering. But dressing from a different era can also simply be fun –– especially when you’re bored during quarantine and can’t hang out with your friends. In a world that can feel like a 24/7 dumpster fire, “Fashion trends are something we can get inventive with and sort of let’s us forget about our problems,” explains 23-year-old Yulissa Corral.
Sixteen-year-old Emily Shapton adds that while she admits she’s unsure why the finance-dad trend is so popular, she’s been drawn to it since it took over.
“What I love about it is the different layers, you have the formal mixed with the informal, with the collared shirt under the sweatshirt along with a short skirt, which helps it look youthful,” she says. “Formalwear has never been something that appeals to teenagers, but now that we have an option that would actually be acceptable in a workplace or school environment, people are looking at this style and making it their go-to look when going out.”
Corral echoes a similar sentiment, saying that while she doesn’t know why this trend is happening right now, she fully endorses it.
“We have to let fashion thrive, prosper, and evolve, especially second-hand fashion, because it’s economically better and you help the local second-hand fashion shops stay open!” she says. “So you wear those white tennis skirts and vests, and a mask of course, and you keep on being the best version of yourself because it’s a vibe, babe.”
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