Every summer vacation, whenever Tom Holland and his three younger brothers were causing a ruckus around the house, his mother would shove the boys out the door with a simple directive: Just go to Wimbledon! Holland grew up—and still lives today—in Kingston upon Thames, a London suburb just 10 minutes up the road from the All England Lawn Tennis Club, the storied grounds of the world’s oldest tennis tournament. For all its history and prestige, Wimbledon ranks among the most egalitarian of sporting events for attendees: If you miss out on tickets, the vast majority of which are distributed through a public lottery system, you’re welcome to wait in the famous Queue outside the gates for rolling access to the grounds. That’s where the brothers Holland would spend their days, often nabbing a chance to catch a few live matches inside. “Back then, we really just wore whatever was clean,” Holland told me last Saturday at a Chase Travel party a few blocks from the tournament, where the actor was promoting his nonalcoholic beer line BERO. “A football shirt and shorts or something like that. Wimbledon is such a family-friendly event, especially in the smaller courts where you can just walk around.” That’s probably a wholly different vision of Wimbledon than the one you’re used to seeing on TV or your feeds. Tennis style has been having “a moment” for several years now, thanks in part to smash movies like Challengers and red-hot labels like Miu Miu sending cable-knit vests and pleated skirts down the runway. The birthplace of that look is the All England Club, where finely attired British royalty and A-listers sit in the Centre Court stands as the game’s greatest players take each other on while wearing pristine whites. All of that tradition and pageantry remains very much a thing. Bob and Mike Bryan, the twin American brothers who raised three Wimbledon doubles trophies during their record-breaking careers, recall occasionally being chastised by officials over the tournament’s decree that players don entirely white gear. (It was seen as a major concession when Wimbledon announced, in 2023, that women would be permitted to wear dark undershorts underneath their white skirts.) “You don’t screw around with the rules,” Bob explained to me. “A couple times we walked out there with a little bit of color on our shirts and within seconds you have a guard with a walkie talkie pulling you off the court.” Rather than finding the regulations stifling, though, the Bryans say most players relish the tournament’s commitment to preserving its time-honored aura. “The rules just add to the mystique, right?” Mike said. “That’s what the players really love when they walk into Wimbledon. You see the old buildings, all the line judges dressed in the green on the wall, the lack of corporate sponsors along the back of the courts. It’s just a classic, clean look, and it never disappoints. When you walk through the gates you always get goosebumps.” Wandering around the grounds myself on Saturday, during Wimbledon’s third round, I was struck by just how relaxed the vibes were. Maybe it’s because they’ve had 148 years to work out the kinks, but everything simply flowed better than at any American sporting event I’ve ever attended. The lines for ticket holders moved quickly and efficiently. The refreshment offerings were a step up from your average ballpark dog and overpriced Bud Light—those fabled Wimbledon strawberries, picked locally every morning at 4 a.m., were as luscious as advertised—but more importantly, guests are allowed to bring their own food and beverages in with them, allowing for charming picnics on the grounds’ famed Henman Hill (and the occasional umpire warning about popping champagne during gameplay). The merch was sublime, from the luxurious Ralph Lauren-designed capsule collection to the more affordable standard-issue hats and polos. And then there were the spectators’ actual clothes. While there’s no official dress code for general-admission guests—though men seated in the Royal Box or visiting the members-only clubhouse are expected to wear a jacket, trousers, and tie—the vast majority of fellas I saw walking around the concourses and seated in Centre Court saw fit to dress smartly. Sure, there were still plenty of hoodies and jeans on display, but more often than not I clocked men in sharp suits, jaunty sport coats, or, at minimum, breezy linen button-ups and crisp trousers. None of it registered as costumey or affected, though, the way the big hats and pastel blazers sometimes do at the Kentucky Derby. It just felt natural, at ease, real. “I was surprised to see that the atmosphere isn’t stiff,” agreed the fashion writer and brand consultant Zach Weiss, “which I think I was sort of expecting with all of the blazers and ties running around. It's just as convivial and fun as the US Open, just not so rough around the edges.” Weiss, who was also at the Chase Travel event to debut his new collection of Wimbledon-inspired leather goods with George Cleverley, is certainly no stranger to New York’s Grand Slam—he once notoriously appeared in the foreground of several much-publicized paparazzi shots of Timothee Chalamet and Kylie Jenner canoodling at Arthur Ashe. But this was his first time at Wimbledon, and the menswear on offer didn’t disappoint. “I think for an American going to Wimbledon, the dressing up is a sort of a novelty experience that verges on cosplay, but it’s very real to the Brits,” he said. “There’s not such a push for informality or comfort, which I love. It’s the only tournament where a good cross section of the crowd collectively maintains the age-old traditions, and that includes getting dressed up.” Of course, the expectation for sartorial splendor has also made Wimbledon one of the most thrilling celeb-spotting affairs on the planet, with an eclectic mix of stars (and their stylists) each interpreting the tournament’s traditional codes to varying degrees of success. Some are regular pros at the posh look (David Beckham), while others you’re just shocked to see in a suit at all (Dave Grohl). According to the celebrity stylist Warren Alfie Baker—who dressed Glen Powell in a Prince of Wales-checked Brunello Cucinelli suit on Saturday, and then put Andrew Garfield in preppy alabaster Ralph Lauren the following day—the goal is to “achieve an effortless chic” while “respecting the rich traditions.” Since graduating from babysitting his brothers in the Queue to movie stardom in the Centre Court stands, Tom Holland’s Wimbledon ensembles have undergone a similarly dramatic evolution. In 2018, just a couple of years into his run as Spider-Man, he appeared at the tournament in a slickly tailored Ralph Lauren Purple Label suit—a long way from the soccer kits of his youth. But when he popped back up at the Championships on Tuesday, he did so in a roomy pink JW Anderson button-down and wide-leg jeans, which seemed to reflect both his recent turn toward a looser, more casual style and a greater ease with himself and fame in general. “I like to be comfortable, but I also really take pride in being smart,” Holland explained. “So Wimbledon is the perfect kind of combination of both of those things.” When I asked for his favorite Wimbledon look of all time, Holland grinned wide. “Zendaya wore that Ralph Lauren suit a couple of years ago,” he said, “and she just looked so beautiful and so at home. It meant so much to me for her to be in a place that I call home and look like such a part of our community.” That sense of effortlessness was a recurring theme among the folks I spoke with. “As always, I felt like the older guys nailed the look,” Weiss said. “There were plenty of famous faces, fully styled, but the seasoned pros always make it look easy. I saw one man in particular in a full white linen suit, a Panama hat, and an incredible pair of two-tone Oxfords that looked like they had already been to Wimbledon for decades. That’s the sort of patina and ease you can’t buy.” Ultimately, the coolest thing about Wimbledon and its signature style is the sense of constancy it imparts. “Our mom [Kathy Blake] played at Wimbledon in the ’60s, and she had to adhere to the same rules as today,” Mike Bryan said. “All those little quirks just make you feel like you’re part of a long lineage of champions. If they put the modern pictures in black and white, you probably wouldn’t be able to tell the difference between matches played in the 1930s and today.” He’s right. While I got to watch plenty of scintillating tennis on Saturday—with rising stars like Jannik Sinner and generational icons like Novak Djokovic cruising to victory on Centre Court—the thing I’ll remember most about my visit to the All England Club was a quieter moment in the Kenneth Ritchie Wimbledon Library, tucked away inside the tournament’s on-site museum. Save for a couple of gossiping librarians, my wife and I were the only ones inside the deeply Wes Anderson-esque space. We flipped through Wimbledon programs from the ’40s, the ’90s, the 2010s. In every decade, the spectators in the photos were all dressed to the nines—and, more importantly, dressed like themselves.