The 12 Boldest U.S. Open Player Looks That Defied Convention Throughout the Years

Since 1881, the U.S. Open has been one of the most prestigious tennis tournaments of the year.

Players often opt for classic tennis whites, athleisure, or performance-driven ensembles designed for the court.

InStyle looks back at the moments professional athletes refused to play it safe with their on-court style.

Ah , the U.S. Open . Dating all the way back to 1881, the buzzy tennis tournament has become one of the biggest sporting events of the year. Today, the action unfolds at the Arthur Ashe Stadium in Queens. It's also the time where we overuse the term " tenniscore ", break out our preppiest pieces, and hunker down for some seriously good tennis. And of course, the world's best players prepare more than just their game for a tournament like this. Their ensembles have become part of the spectacle, too. While tennis style has long been associated with crisp whites , athleisure, and performance-minded pieces , the U.S. Open has also given players plenty of room to experiment—and some have taken full advantage.

Over the years, a handful of athletes have refused to play it safe, making bold statements with their on- and off-court style. Back in the '90s, when tennis style tended to skew a bit more conservative, Andre Agassi and the Williams sisters weren't afraid to push the style boundaries during their matches. Fast forward to 2025, and Naomi Osaka took the bag charm craze to another level with custom Labubus .

To get in the spirit this year, we're revisiting 12 of the boldest looks to ever hit the U.S. Open.

John McEnroe wasn't afriad to show a little leg at the 1980 U.S. Open. The tennis star took to the court in seriously short shorts paired with a classic polo and his signature headband, creating a look that feels quintessentially '80s today.

Andre Agassi's Mullet and Neon Look (1990)

Andre Agassi brought rebellious energy in 1990, pairing his signature mullet with a bold neon ensemble that stood out against tennis's traditionally preppy aesthetic. With bright colors, denim-inspired details, and plenty of attitude, his look helped usher in a more expressive era of on-court style.

Venus and Serena Williams made their beaded braids a signature part of their early careers, bringing a distinctive sense of personal style to the court. While the beads occasionally sparked debate over the noise they made during play, the look ultimately became an iconic part of the sisters' legacy—and helped broaden perceptions of what a tennis star could look like.

Serena Williams turned heads in 2002 when she stepped out in a skin-tight, black Puma catsuit that looked like more of a fashion statement than traditional tennis attire. Paired with pops of light pink sweat bands, the daring look became one of her most memorable on-court outfits.

Serena Williams brought street style to the court at the 2004 U.S. Open, sporting a Nike denim-look mini skirt paired with a studded black tank and matching accessories. Looking back, the denim, studs, and body-skimming silhouette feel totally Y2K-coded.

Maria Sharapova's Swarovski Crystal Dress (2006)

Maria Sharapova brought some serious sparkle to the 2006 U.S. Open in a black Nike dress embellished with Swarovski crystals. Inspired by New York City at night, the glamorous design was a fitting choice for the tournament's evening matches.

Bethanie Mattek-Sands' Leopard Print (2007)

Bethanie Mattek-Sands went wild at the 2007 U.S. Open, hitting the court in a leopard-print ensemble complete with a matching headband. Known for her unconventional approach to tennis fashion, the American player proved she wasn't afraid to stand out from the competition.

Roger Federer's "Darth Federer" Look (2007)

Roger Federer embraced his dark side in 2007. He stepped onto the court in an all-black Nike ensemble that quickly earned him the nickname "Darth Federer." Complete with black sneakers and a matching headband, the monochromatic look was a sleek departure from traditional tennis whites.

Caroline Wozniacki's Mesh Stella McCartney Dress (2010)

Caroline Wozniacki put a fashion-forward spin on tennis wear in a Stella McCartney for Adidas dress featuring sheer mesh detailing and a super-short silhouette. The unexpected design brought a little edge to the court while still feeling sporty.

Carlos Alcaraz's Sleeveless Basketball Jersey (2023)

Carlos Alcaraz brought a basketball-inspired edge to the 2023 U.S. Open, competing in a sleeveless Nike top that resembled a jersey. Paired with red shorts, the sporty look felt more NBA than country club.

Brat summer carried on at the 2024 U.S. Open, where Naomi Osaka stepped onto the court in a custom Nike look featuring a bright green dress and an oversized bow. Designed in collaboration with Yoon Ahn of AMBUSH, the playful ensemble mixed coquette details with performance tennis wear.

Naomi Osaka's Blinged-Out Labubus (2025)

Naomi Osaka took the Labubu phenomenon courtside (usually attached to her tennis bags) at the 2025 U.S. Open with custom, blinged-out versions of the viral bag charm by New York-based accessories brand A-Morir. Dubbed "Lablingblings," the 3-D printed charms feature approximately 3,000 hand-applied crystals, taking one of 2025's biggest trends to dazzling new heights.