From Taylor Swift to Zendaya: The Celebrity US Open Looks We'll Still Be Referencing for Years

There are plenty of sporting events that double as unofficial fashion weeks—the NBA tunnel, Wimbledon, basically any Formula 1 paddock—but few have mastered the celebrity style spectacle quite like the US Open. Every late summer, the stands at Arthur Ashe Stadium become their own kind of runway, with actors, musicians, models, and fashion-world favorites turning up in outfits that can occasionally rival whatever is happening on the court. (Sorry, tennis fans!)
While the US Open has become an especially buzzy fashion moment in recent years, its best celebrity looks have been building for decades. Think Barbra Streisand's all-whir and Taylor Swift leaning into the preppy Americana codes that feel practically made for an afternoon in Queens. The beauty of US Open style is that there isn't really one uniform. You’ll spot everything from immaculate tailoring and little white dresses to denim, baseball caps, and the kind of deceptively casual outfits that inevitably end up all over our mood boards.
In honor of another US Open season, we're looking back at the best US Open celebrity looks of all time—the outfits that captured their era perfectly, set off trends of their own, or simply remain just as good years (and sometimes decades) later. Consider this the celebrity style equivalent of an instant replay.
Britney Spears at the 1999 US Open.
Taylor Swift at the 2024 US Open.
Mary-Kate and Ashley Olsen at the 2004 US Open.
Barbra Streisand at the 1992 US Open.
Serena Williams at the 2004 US Open
Anna Wintour at the 2005 US Open.
Zendaya at the 2022 US Open.
Kendall Jenner at the 2022 US Open.
Andre Agassi at the 1988 US Open.
Serena Williams at the 2018 US Open.
Naomi Osaka at the 2024 US Open.
Roger Federer at the 2014 US Open.
Maria Sharapova at the 2007 US Open.

Ana Escalante is an award-winning journalist and Gen Z editor known for her sharp takes on fashion and culture. She’s covered everything from Copenhagen Fashion Week to Roe v. Wade protests as the Editorial Assistant at Glamour after earning her journalism degree at the University of Florida in 2021. At Who What Wear, Ana mixes wit with unapologetic commentary in long-form fashion and beauty content, creating pieces that resonate with a digital-first generation. If it’s smart, snarky, and unexpected, chances are her name’s on it.