Why Is Everyone Obsessed with Josh O’Connor’s Challengers Outfits?

First-time costume designer Jonathan Anderson explains how he enhanced the “sex appeal and attraction” of O’Connor dirtbag tennis pro, and O’Connor weighs in on his character’s starring shorts.
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Courtesy of Getty Images / Photo illustration by Armando Zaragoza

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What makes Josh O’Connor’s outfits in Challengers so alluring?

On paper at least, it’s not obvious. When we meet dirtbag tour pro Patrick Zweig (played by O’Connor) in Luca Guadagnino’s sweaty tennis ménage à trois, he is in the finals of a dinky regional tournament, wearing a kit that looks like it was pulled off the top of the laundry pile. We soon realize that, indeed, Patrick’s black muscle tank and plaid Nike athletic shorts were pulled out of some crevasse in his car, where the one time tennis wunderkind has been living.

And yet Patrick’s ratty tournament getup is starting to feel like one of the most important menswear moments of 2024. Ever since the trailer dropped, there has been Sahara levels of thirst around Challengers and the racy love triangle between the film’s three tennis stars, played by O’Connor, Zendaya, and Mike Faist. But at least some moviegoers left the theater thinking less about what might happen in the locker room after the cliffhanger ending and more about the choices made by the costume designer, Loewe creative director Jonathan Anderson.

Jonathan Anderson's sketch of Patrick Zweig's opening outfit.

I for one am hesitant to admit how much time I spent last weekend scouring eBay for those long-out-of-style plaid shorts, Trent Reznor & Atticus Ross’s techno soundtrack thumping in my headphones. According to vintage dealer Bijan Shahvali, the shorts likely date to Andre Agassi’s reign and are therefore vanishingly rare. “Brother, I too have been searching for those shorts,” he replied when I asked. I heard from several other Challengers-goers fiending for the shorts. “I loved them,” said Racquet founder Caitlin Thompson. Patrick’s outfits, Thompson added, “are the moment” right now, precisely because they feel so out of place in the sport’s classy current landscape. “Tennis hasn’t really had a dirtbag boyfriend look since bandana Agassi,” she said.

It’s not just the plaid shorts that captivated audiences: a colleague admitted that she was on the hunt for the impeccably-random Mizuno trainers O’Connor wears in several scenes. Meanwhile, fans have made countless bootleg versions of the “I TOLD YA” graphic tee worn by Patrick (and stolen by Zendaya’s character) throughout the flick. GQ has even speculated that Patrick’s normie Nike Killshot sneakers might be due for a comeback. (Anderson built every element of the characters’ wardrobes, mixing off-the-rack and custom pieces.)

It’s one thing to leave, say, Phantom Thread feeling sartorially inspired, and another thing to spend hours trying to track down specific, obscure costume pieces from an era of bad tennis looks worn by a character who, we are led to believe, doesn’t care what he wears at all.

Patrick, right, wearing his tiny gold watch.

Niko Tavernise

Which is precisely why Patrick Zweig is an unlikely style touchstone for our time. In an image-saturated world where everyone (including you and me) tend to over- rather than under-obsesses about the things we wear, Patrick dresses with complete, coherent ease. Unlike the successful and manipulative Tashi Duncan, played by Zendaya, Patrick doesn’t wear fashion brands. He is in fact anti-fashion. His clothes might be styled in a knowingly funky way, but it looks like everything he owns has been in his life forever. When Patrick faces off against Faist’s Art Donaldson, the contrast couldn’t be more clear. Art, a polished grand slam winner, wears whatever spotless whites his sponsors give him. He is a square. He’s got the Grand Slam trophies and the girl (Tashi), but Patrick is the guy everyone wants to be. And, not coincidentally, the guy everyone wants to dress like.

Character building is second nature to Jonathan Anderson, better known for his uber-zeitgeisty runway collections at Loewe and JW Anderson. Challengers marks his first costume design credit, but at his day jobs Anderson harnesses the stereotypes of normal clothing to make bold conceptual statements. And he is particularly good at giving clothing an aphrodisiacal quality. Anderson’s Loewe men’s show in January was laden with kinky details like seductively unbuckled blue jeans and white dress shirts tucked into gray sweatpants that seemed hastily pulled on, all suggestive of the e-boys and OnlyFans models who populate our social media landscape. Like a great filmmaker, Anderson uses layers of artistic narrative to alter our perceptions of the everyday—in this case, everyday garments.

As Josh O’Connor himself told me in a recent interview for a profile of Anderson, the designer’s understanding of the subtleties of regular-degular clothes was key to unlocking Patrick’s character. The actor described a scene set in 2019 in which Patrick, who’s from a wealthy family but is bumming around on the triple-A Challengers tour, tries to talk a receptionist at a cheap motel near a tournament in upstate New York into giving him a free room. Patrick is out of cash and down bad. As my Vogue colleague Jose Criales-Unzueta puts it, “You can tell he… smells.” But his clothes—a tight windbreaker, leg-revealing running shorts, and cooked Gola trainers—suggest a more interesting story.

“Much like JFK Jr. when he was younger, there was an effortlessness in his wardrobe,” says Anderson about Josh O’Connor’s character.

Metro Goldwyn Mayer Pictures

In a wardrobe fitting for the scene, Anderson pulled out a pair of purple-ish nylon shorts. “They're not so short that it's insane. But they are short shorts,” O’Connor said. “And I remember looking at Jonathan and being like, Really? I don't know. I'm not sure about this.” It sounds like a small thing, but the shorts are a critical element at a juncture in the film where Guadagnino needs to establish Patrick’s illicit magnetism. He could be wearing just about anything in that scene, and Anderson designed an outfit that flashes the character’s natural athleticism and, based on the volume of horny tweets about the shorts, his even more natural sex appeal.

Anderson convinced O’Connor to wear them. “This is the amazing thing about Jonathan,” O’Connor told me. “I remember him being like, Patrick is all about sex. He's all about being sexual and trying to entice people. And so he would just put these on. He'd actively seek out shorts like this. And ultimately that was a garment that I thought was so perfect. The fact that Jonathan thought it through in that way was very interesting.”

There’s a model for Patrick in JFK Jr., a figure who made every windbreaker and NYAC sweat-short look like an heirloom, whose All-American jock style inspires to this day a strange combination of lust and emulation. In an email, Anderson explained further: “Patrick as a character was born into a very wealthy family, so my take was to highlight a sense of nonchalance towards his appearance. Much like JFK Jr. when he was younger, there was an effortlessness in his wardrobe,” the designer said.

By now you’ve probably heard about the very-Andersonian Easter egg in Challengers. The gray “I TOLD YA” gym tee that Patrick steals back from Tashi is a recreation of a tee that JFK Jr. wore in the ’80s. Though the slogan is left unacknowledged in the film, it serves as a not-so-subtle reminder that Patrick might be down, but never out. And like the tiny, leather-banded gold watch strapped to his wrist as the film bounces between decades, the tee is broken in by time. These tiny details elevate Patrick’s slovenly sportswear, and further emphasize his powers of seduction, according to Anderson. “Despite Patrick’s [low] status in the tennis world, you’ll see incredible aged and timeless pieces within his wardrobe which enhance the sex appeal and the attraction of his character,” Anderson said.

Barring a surprise reissue by Nike, right now only Anderson knows where to get the shorts. “What hurts the most,” rued someone on X, “is that challengers was shot so long ago that the plaid Nike shorts Patrick wore are wiped from human civilization.” There are, however, a couple sizes of Patrick’s Mizuno trainers floating around in the e-commerce ether. But if you really want to emulate O’Connor’s sweaty Challengers sleaze, Anderson has you covered. On Thursday, Loewe released a luxe version of the “I TOLD YA” tee.

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