The Cool Girl’s Guide To Wimbledon Dressing

The overlap between fashion and sports has become increasingly more prevalent in recent years, whether it’s through luxury tunnel outfits donned by superstar NBA and WNBA players, brands investing in the ever-growing Formula 1 craze, or soccer jerseys becoming a summer wardrobe staple thanks to the World Cup. But there’s one sport that’s historically had style at its forefront: tennis. With plenty of major brands — like Off-White, Louis Vuitton, Miu Miu, Gucci, and more — devoted to consistently dressing top players, it’s no surprise that the annual tennis competitions attract a fashion-forward crowd.

This is especially true for Wimbledon — the oldest, and arguably most reputable, tennis tournament in the world. The event takes place every year from late June to early July in London, naturally pulling a slew of typically very posh, high-profile celebrities to sit courtside to watch stars like Serena Williams and Naomi Osaka. Regular attendees of the matches include Anna Wintour, Nicole Kidman, Cate Blanchett, Alexa Chung, and The Princess of Wales, Kate Middleton. And now, over the last few years, a new generation of famous faces has been embracing the swanky athletic affair.

In 2024, Zendaya attended with Ralph Lauren as part of her Challengers promotional run; at the 2023 event, Ariana Grande made one of her first public appearances as a Glinda-fied blonde; and in 2024, Charli XCX brought a touch of Brat to the occasion. Safe to say, Wimbledon is a certified hot spot for It-girls everywhere.

In preparation for the impending cool girl gathering (and actual tennis matches, of course), we’ve compiled our favorite Wimbledon looks from years past and found the perfect pieces to help recreate each one. Scroll on to see them all.

Shirt Dresses

Take it from Olivia Rodrigo and Nicola Coughlan: shirt dresses are the easiest way to give pristine, polished energy while putting very little effort into your look. With a flattering silhouette, a pressed collar, and some fun button details, a well-made shirt dress will impress both the most traditional ticketholder and fashion fans. To add a little edge to the classic design, pair it with a statement bag and a stylish set of sunglasses, just like the “Drop Dead” singer.

Sideline Suiting

With Wimbledon being such a prestigious event, it makes sense that many match-goers get a bit more dressed up than they would for, say, a basketball game in the United States. But being more buttoned-up doesn’t have to translate to boring. As expertly modeled by Princess Diana in the 1990s, a good suit — accompanied by the right accessories — can make you look both sophisticated and on-trend. Zendaya offered a more menswear-focused take in 2024, pairing her crisp double-breasted suit dress with a striped dress shirt and navy knit tie.

Summer LBDs

For those more interested in presenting an edgier vibe in the stands, look no further than Charli XCX’s most recent Wimbledon appearance for some Saint Laurent-fueled black summer lace inspiration. Darker shades are still perfectly acceptable in warmer weather, especially if you balance out the deep hue with a slinky style — à la Victoria Beckham in 2013 — or keep things cool with plentiful cutouts. Take a note out of both Brits’ playbooks and accessorize with blacked-out lenses and leather footwear for some added punkiness.

Simple Slips

With temperatures in Europe reaching record highs this month, it’s more compelling than ever to simplify our outfits, leaving looks as lightweight and layerless as possible. A no-fuss slip dress is the ideal summer staple thanks to its flattering cuts and typically loose, breathable fabric. Although the garment itself is minimalistic, it can easily be zhuzhed up with some stacked jewelry, a contrasting bag, or a bold color choice, just as Daisy Edgar-Jones and Lila Moss have demonstrated.

Statement Sporty Jackets

Sometimes dressing for the occasion can include a little bit of chic cosplay. Evoke the athlete aesthetic by sporting (see what I did there?) a stylish piece of activewear, such as a retro windbreaker, varsity, or bomber jacket. Tennis WAG-in-residence Paige Lorenze modeled a very ‘80s yellow-and-black New Balance funnel-neck design back in 2024, complementing it with gold hoops and rose-colored sunnies. Jodie Turner Smith offered a more maximalist approach to the trend, wearing a rich purple Ralph Lauren look covered in various embroideries and accoutrements.

Laid-Back Linens

Linen dresses and sets are a sure thing for any summertime outing. They’re easy to throw on, feel as comfortable as pajamas, and serve as a great blank canvas for accessorizing. Whether you’re looking to dive into fun hat options this season — like Keira Knightley — or go the quiet luxury route like Sabrina Elba (her matching two-piece ensemble was mainly a backdrop for her Margaux bag from The Row), there are endless ways to decorate a laid-back linen look.