Serena Williams Outfits That Totally Fell Flat

Serena Williams is a fashionista whose often quirky outfits will go down in history in the sports world and far beyond. She has such a passion for fashion she's even attempted to help others score her bold and fearless style, creating a plethora of clothing collections for women and children. But, just like many stars with a penchant for out-there outfits, she's made a few questionable choices. Not that Williams is bothered if we don't like her look, though. 

"I think being on worst dressed lists is important. I've loved every style that I've made and you know, you don't love them looking back all the time, but I appreciate them," she told People in 2024. She'd also shared a similar sentiment with People 15 years earlier, telling the outlet, "I've been on the worst dressed list several times, and I don't care. I like what I like, and if I feel good wearing something, I'll wear it."

But while we love athlete's refreshing take on dressing for herself and staying true to her style (almost as much as we love this celeb's honesty about wearing wigs), it's hard to ignore that there are a few times her outfits have fallen totally flat. Williams' style file includes everything from awkward wardrobe malfunctions to poorly tailored numbers that just didn't work.

Any dress that leaves someone open to an unintended wardrobe malfunction deserves an instant spot on a worst dressed list. Serena Williams learned that in 2019 when she stepped out in New York in a blue and white striped shirt dress with red, heart embellishments. Though the garment flattered her figure thanks to its waist-cinching belt and matched her metallic red, pointed toe heels perfectly, the bottom button came undone. That allowed the garment open as she walked, exposing her white underwear. Though Williams handled the wardrobe malfunction gracefully, it forced what could have been a chic style moment to majorly miss the mark.

Serena Williams wore a black-and-white mini dress on the red carpet in 2008, but the lace decolletage, silky waist bow, and her short, vintage-style haircut felt dated and out of step with her experimental style. The lace top had black lines from her shoulders to her chest that ruined the flirty aesthetic over her decolletage, and her pearl jewelry did nothing to make the look more youthful and modern either.

To elevate this outfit, we'd have suggested pairing it with modern, metallic jewelry. The tennis superstar could also have benefited from swapping her clunky, platform pumps for fall 2008's hottest shoe trend, the T-Strap heel, which would have created a more streamline silhouette.

We appreciate that Serena Williams take fashion risks while playing tennis, merging sports and style. But when she posted a snap of herself to TwitPic via X, formerly known as Twitter, in a skin-tight, hot pink catsuit in 2011, it didn't serve a tenniscore summer vibe. Though the athletic beauty looked stunning, the one-piece was totally impractical for a day on the court. The distracting number didn't look like it offered much breathability, which can be dangerous while exercising. Because tennis requires so much movement, the star also risked the unique garment ripping at the seams every time she moved.

Serena Williams turned up the glam with her plunging, light pink gown at the 2003 ESPYs, but it needed more tailoring to truly flatter her figure. The sparkly band sat a little low to highlight her waist and the material over her chest looked too baggy. She could have achieved a cleaner silhouette if the dress had been cinched in and pulled up. Because the material was so delicate, it appeared wrinkled over her stomach and hips, too — never a good look on a big red carpet. However, the shade looked gorgeous against her skin tone and the athlete's bright smile almost (but not quite) distracted her from the dress's issues.

For the premiere of "The Bourne Supremacy" in 2004, Serena Williams (who was in her early 20s) wore an outfit that looked more like a school uniform or costume than a sophisticated, red carpet ensemble. She wore a white shirt tucked into a denim miniskirt, with Y2K trendy, pink, kitten heels, and a chunky tie. The 'fit may not have looked so out of place at a "St. Trinian's" premiere but had no correlation to the action movie, making her look out of place. Williams had so many fierce red carpet looks both before and after this questionable choice, so we were left really scratching our heads over this misstep.