The Group Chat: Classy and grassy

Ready for the pinnacle of summer style? The world’s greatest tennis players are descending upon the All England Lawn Tennis & Croquet Club as Wimbledon — tennis’ third Grand Slam of the year — gets underway this week. But winning on the court is only half the fun — for both players and fans, a major part of attending London’s biggest summer bash is looking the part.

• Today, we’ll dig into the fashion that makes Wimbledon so iconic, from the strict (but recently evolving) on-court dress code, to the unspoken rules in the stands. Aces, incoming.

👗 Let’s start with the prestigious tournament’s mandatory dress code. The oldest tennis competition in the world, Wimbledon has been steeped in tradition since its inception in 1877. Player attire was required to be “almost entirely white” from their first step onto the grass courts — whether they were practicing or playing in a match.

• We’re talking tops, bottoms, dress, shorts, hats, headbands, socks, shoes — everything had to be white (not cream, ivory, or off-white) and considered “suitable tennis attire.” And if you broke those rules, there were consequences.

⏩ Fast forward to 2023, when Wimbledon officials finally updated the dress code, permitting women to wear dark undergarments after years of advocacy from menstruating players.

Spectators are not beholden to the same strict all-white dress code as players, but there is code of decorum for fans attending Wimbledon. “Smart dress” is heavily encouraged, while items like ripped jeans, dirty shoes, and flashy designer logos are forbidden.

• What exactly is “smart dress?” Think polished, classic, elegant — we’re talking a blazer with jeans, a linen midi dress, a matching set…or anything from the latest Ralph Lauren Wimbledon collection, of course.

With that background, here are a few of our favorite Wimbledon looks, on and off the court. Game, set, snatch.

1️⃣ Gertrude Moran, 1950: A player in the 1940s and ’50s who reached No. 4 in the U.S. national tennis ranking, “Gorgeous Gussie” was known for her daring looks, but this one took the cake. Designed by Pierre Balmain himself, this outfit purposefully showed off Moran’s bloomers (aka the shorts under her skirt), a disruptive statement at the time.

2️⃣ Princess Diana, 1995: Lady Di was truly ahead of her time, rocking this timeless butter yellow (the color of the summer!) two-piece set with round sunnies and gold accessories, a ’fit that would slay just as hard in 2025.

3️⃣ Serena Williams, 2004: We could fill an entire newsletter with Serena’s Wimbledon looks, but this Nike gladiator ensemble, complete with a strappy leather skirt, was truly unforgettable.

4️⃣ Roger Federer, 2023: It’s one thing to be the winningest Wimbledon gentleman of all-time — it’s another to be the most stylish. Somehow, Anna Wintour’s bestie, Roger Federer, manages to do both, wearing this sleek cream blazer when he was honored on Centre Court.

5️⃣ Zendaya, 2024: As part of her tennis-inspired press tour for Challengers, Zendaya spent two days at Wimbledon last year, rocking very different, but equally fab Ralph Lauren looks. Tashi Duncan would be proud.