Each July, fashion and sports fans alike turn their attention to Wimbledon to check out the serves on and off court. The trophies are polished. The linens are freshly pressed. And as always, the stakes are high—stiletto height to be exact. From practitioners of classic clothing codes to quiet (or not-so-quiet) rulebreakers, the fortnight becomes more about style points than match points. If we’re calling it like it is: in the court of public opinion, it’s already game, set, match.

The year is 2017. Balayage runs rampant across the locks of 20-something women worldwide, Despacito is the soundtrack of summer, and Alexa Chung is everyone’s moodboard muse. While tennis enthusiasts are all watching the match, fashion fanatics’ eyes are glued on Chung.

In quintessential fashion, she shrugs off the pastel frocks most expected and frequently sported on the All England Club grounds for something, well, chicer. Sashaying past the Pimms Cup stands in a double-breasted pinstripe power suit and polka dotted navy necktie, she effortlessly pairs her Savile Row-meets-Left Bank look with a Jane Birkin-esque woven bag and a well-timed ballet flat. Her signature shag remains perfectly mussed—and yes, balayaged! The internet hasn’t been this collectively smitten since we all reblogged her in a Peter Pan collar. Ah, that’s why they call her an it-girl.

If Alexa brought us back to Tumblr’s golden age, Charli XCX glitches us straight into the hyperpop moment: Brat Summer 2024, to be precise. The knee-high lace stockings with leather slingbacks. The cheeky lingerie peek through. The narrow black rectangular frames. The unapologetic irreverence of it all. Just weeks after releasing the lime green album of the summer (or century, depending who you ask), Charli arrives at Wimbledon looking less like a spectator, more like a headliner. Intentionally out of sync with the white-dress decorum, she makes a statement loud enough to echo across the grass courts: disruption looks good in sheer black crochet! Tradition didn’t stand a chance.

You can’t spell “Wimbledon” without “Kate Middleton.” Freshly out of the aisle of Westminster Abbey, the then-Duchess of Cambridge makes her royal box debut in nothing short of prim, proper, and perfectly on dress code. Regally outfitted in a tiered sleeveless white frock, she blends into the Wimbledon whites as the crown jewel of Centre Court. Her glossy brunette blowout intact, the Duchess pairs the crisp dress with nude pumps, that unmistakable sapphire engagement ring, and a structured clutch tucked neatly at her side. It’s a royal rite of passage for the lifelong tennis fan with a predilection for polite silhouettes and even “politer” applause. The aristocratic trendsetter would go on to be named the official patron of the All England Lawn Tennis and Croquet Club and its unofficial muse. Perhaps she doesn’t follow the dress code, but she is it.

Having just headlined Glastonbury—or “Glasto”, if you’re in the know—Olivia Rodrigo makes a swift pivot from festival grit to courtside polish. Arriving at the iconic English institution in a red-and-white checkerboard button-up dress tweefully fastened *to the top*, she leans all the way into the color palette of berries and cream. It’s giving Wes Anderson ingenue. Her accessories of choice: retro oval sunnies, a red velvet shoulder bag, and British boyfriend, Louis Partridge. Oh, she’s having her Euro summer.

Wimbledon may have its champions, but the real legacy lives in the looks that linger long after match point. The tournament constructs a cultural canon with every lapel and hemline on the hallowed grounds of SW19. From archival references to rule-bending interpretations on tradition, these are the moments that rally through the decades. No umpire required to call that! While there’s no tiebreaker in the arena of fashion, there most certainly are aces.