At Wimbledon, Preppy Style Always Wins

At Wimbledon—the annual tennis tournament held in London, not to mention the oldest tournament in the world—all eyes are typically on the court, where pro athletes such as Roger Federer, Martina Navratilova, and Serena Williams have all played and won titles. But in the audience stands, there are also plenty of sights to behold. Celebrity spectators are known to dress to the nines for the games, bringing forward their most polished—and preppy—ensembles for the occasion. And in honor of this year’s Wimbledon, which begins on Monday after this week’s qualifiers, Vogue is taking a look back at some of the very best celebrity style moments from over the years.

Throughout Wimbledon, which kicked off back in 1877, it’s been a tradition for royals to attend—and many of them have delivered some of the tournament’s most memorable ensembles. Take Princess Diana in the early ’90s, who often attended the games wearing her signature big-shouldered sundresses. In more recent years, Kate Middleton has often delivered chic ensembles at Wimbledon; Some of her most memorable looks include the striking green Emilia Wickstead dress she wore in 2019, which nodded to the tournament’s signature color scheme (green and purple). That same year, Middleton attended with Meghan Markle, who wore a crisp white Givenchy shirt and a printed, pleated Boss skirt. 

Royalty aside, Hollywood A-listers have also made appearances at the Wimbledon games—and in equally-stylish outfits, too. Sienna Miller has been a regular at the tournament, with the striped Ralph Lauren jumpsuit she sported last year certainly nailing the easy, summery vibe that’s often embraced at Wimbledon. Stars have also put their own stamp on preppy dressing in more unexpected ways. Janelle Monae’s appearance at the 2019 games—in a striped Thom Browne look including a button-up jacket, pleated skirt, and knee-high socks—was a head-to-toe take on the aesthetic. That same year, Kendall Jenner opted for minimalism, in a Polo Ralph Lauren fit including a blue button-up and white mini shorts. 

This year, we will likely see a grand return of the Wimbledon-approved sweet sundresses or smart cream blazers—and we simply can’t wait to see what stars will step out in, too. After all, it’s clear that the event has become just as much about the spectators style as it is the matches.

Below, find more of the best celebrity style moments from Wimbledon.