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Is Dressing Like JFK Jr. the Key to Getting a Girlfriend?

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Photo: FX

This article first ran in The Cut’s Saturday newsletter, Personals, which features new sex and love stories — and date-wanted ads from interesting single people — every week. Sign up to receive the next issue in your inbox.

It’s the first over-60-degree day in New York, and the city’s women are ready to thaw out. Gathered in the shadow of the Washington Square Park arch are hundreds of 20-something women in their finest turtlenecks, headbands, and oval-shaped sunglasses for a John F. Kennedy Jr. look-alike contest, the latest in a string of engineered-to-be-viral doppelgänger meet-ups in New York. Many among the crowd aren’t coy about what brought them out. “I came here looking for a husband,” said Hannah Engel, a 25-year-old wearing a striped J. Crew roll-neck sweater and carrying a sign reading “Winner to Claim Prize at My Apt.”

Ever since Love Story, the Ryan Murphy–produced series about JFK Jr. and Carolyn Bessette, premiered last month, it seems like everyone is going Kennedy-core. If you’re suddenly seeing men on Citi Bikes wearing ties with jeans and backward hats, this is why. Across the city (and on social media), men are copying JFK Jr.’s balance of old-money prep and sporty casual, which made him one of the biggest men’s style icons of the ’90s. It’s also sparking a resurgence in Kangol hats — during a walk around McCarren Park recently, I spotted two guys wearing them backward. On TikTok, the trend is straightforwardly associated with impressing women. “Dressing like JFK Jr. to find my Carolyn Bessette,” one man, a 27-year-old in advertising named Joshua Elliott, said in a video showing off his outfit, which included the telltale hat.

Is all this Waspy peacocking hitting with women in the way men hope? Shelby Fauvel-Decrombecque, a 30-year-old biologist who posted a viral TikTok about this phenomenon, told me it was shocking to see guys in Jr. drag in the wild. While at a friend’s birthday party on the Lower East Side last month, she said, “I thought I was hallucinating — all of a sudden, there were about five guys in Kangol hats.” Despite her initial shock, Fauvel-Decrombecque had to hand it to them for committing to such a statement piece. “It’s fun to see people taking a risk; I thought they looked great,” she said.

@shelbs.christine

Sorry to these guys, couldn’t help it. You look great!

♬ american wedding - 🎵
@stephhpekic

Sorry to whoever this guy is but I couldn’t help myself it was too funny #lovestory #jfkjr #cbk #foryou

♬ origineel geluid - kenji

Men who put in the effort to wear their finest dress shirts and medium-wash denim will be rewarded, from what I saw at the look-alike competition. While only eight men showed up to vie for the prize, hundreds of women were there to cheer them on. “It’s, like, 95 percent women with their phones out!” a 26-year-old named Annie Burns, who works at a perfume company, said as the JFK Jrs lined up for judging. “The ratio was worse than, like, the bars,” a 23-year-old named Jen told me. “I thought Jack Schlossberg might be here,” Gabrielle Naucke, a 24-year-old working in PR, said. (He was not.) A few, apparently expecting stiff competition, put in extra effort to appeal to the contestants: a woman on TikTok said she brought a basket of homemade banana bread to give out to the men.

Perhaps one sign of this dating tactic’s effectiveness: Many of the look-alikes told me they were taken and had help with picking out their competition outfits from the women in their lives. “Really, my girlfriend kind of just dressed me like a Ken doll,” a 24-year-old named Joseph Frierson, a master’s degree student at NYU, said. At least a couple of contestants, including the winner, were single — one, 24-year-old influencer Enny Radoncic, said he welcomed any prospective ladies sliding into his DMs. Still, the look-alike contest didn’t seem to be very successful as a pickup spot; if the unbalanced gender ratio wasn’t detrimental enough, things got interrupted by a “Make Iran Great Again” rally minutes after the competition ended.

Photo: Julia Reinstein

While the women I spoke to acknowledged that not everyone can pull off a Kangol hat (the secret, it seems, is being extremely hot), most of them were there for any man trying out something new with his clothes. “It’s good that men are like, Hmm, maybe I should think about my style,” said a 29-year-old named Fenella Theis, who works for an auction house. “A little bit of rizz — a little bit of putting effort in your wardrobe — is attractive to women.” Shelby, the woman who spotted the group of hatted men at the bar, wondered whether dressing this way has less to do with getting dates and more about the boost of confidence that comes with putting that shit on. “If you’re doing it in the pursuit of getting a girlfriend, then maybe it’s seen as a little bit cooler among your peers, like, Oh, I’m not taking this too seriously, guys, it’s just so I can get girls,” she said. “Maybe it gives them the safe space to take a fashion risk.”

At least one JFK Jr. Jr. insisted he’s in it for love. Joshua, the 27-year-old TikTokker with the Kangol hat, couldn’t make it to the competition, but he told me his video “hasn’t helped at all” with finding a date. “There’s been some nice comments and some slide-ins, but nothing serious,” he said. CBK wannabes, ball’s in your court.

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