“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.”
Glen Powell
Neil Mockford
Monica Barbaro and Andrew Garfield
Neil Mockford
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.”
Tom Holland at Wimbledon in 2018…
Neil Mockford
…and again in 2025.
Karwai Tang
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.”
