These Celebs Might Be The Worst-Dressed In ESPY Award History
The worlds of sports and fashion have always been closely connected, whether it be through collaborations or endorsements. NBA player Michael Jordan was able to afford his million-dollar wedding in part due to his revolutionary 'Air Jordan' collaboration with Nike back in 1985. Naomi Osaka is another fashion-forward athlete, and she's brought Japanese designers to the forefront since the 2024 US Open. Even former Patriots Quarterback Tom Brady strutted his stuff on the runway at the Gucci Cruise show in 2026. While the 2020s are shaping up to be one of the most fashionable decades for sports, some athletes still miss the mark with their style.
When gathering to celebrate the best of the best of any industry, it's natural to expect to see everyone dressed to the nines. But at the Excellence in Sports Performance Yearly Awards (ESPYs), not every look can be a home run. It's by no means exclusive to athletes, as you'll find plenty of actors, singers, and reality stars walking the red carpet alongside Olympians and sports icons.
Many of the worst-dressed celebs at the 2026 MET Gala failed to adhere to a specific theme, but with its informal black-tie dress code, the ESPYs have been a fashion free-for-all since 1993. Some celebrities thrive with this creative freedom, but others need some style discipline. With the 2026 ESPYs set for July 15, it's worth remembering the worst-dressed moments from the event's red carpet in hopes that this year's attendees won't make the same mistakes.
Odell Beckham Jr.'s front-pouch was a little too marsupial
New York Giants wide receiver Odell Beckham Jr. is typically quite the looker — even catching Kim Kardashian's attention for a brief fling from 2023 to 2024. She must not have seen his disastrous 2019 ESPYs look, as the NFL player got his fair share of mockery for the kangaroo-like pouch on the front of his khaki Prada set. The overly utilitarian feature on the front of the vest did no favors for the athlete's physique, and especially in comparison to his glamorous co-presentor, Gabrielle Union, the look was a total fumble.
Thankfully Jason Oppenheim and Mary Bonnet weren't selling their EPSY looks
The Netflix original "Selling Sunset" is arguably one of the platform's most iconic reality shows, centering around twins Brett and Jason Oppenheim and the glamorous realtors who work at their firm. But one of the show's realtors, Mary Bonnet, was one of the worst-dressed stars at the 2024 ESPYs. Posing with Jason on the red carpet, Bonnet's baffling lacy corset gown looked like it needed a good steam and tighter cinching. However, Jason also deserves to be ranked among the worst for his strange draw-string sweat-trousers and matching blazer over a plain white tee.
Alison Brie's floral Cavalli number was a total mismatch
"Glow" star Alison Brie has always had a diverse sense of style, rocking bold patterns and leather looks alike. However, the two-piece Roberto Cavalli outfit she wore to the 2022 ESPYs was simultaneously too much and lackluster. The black garter buckles on her mini skirt were incredibly punk, but the pastel leather flower appliqués felt like a total mismatch. Thankfully, Brie got back on track at the 2025 ESPYs with a playful, bright-blue mini dress, and if she decides to wear Cavalli again, we hope she sticks with the label's signature animal prints.
Alex Morgan's frumpy silver bodice should have earned her a yellow card
U.S. Women's Soccer player Alex Morgan won the ESPYs 'Icon' Award at the 2025 ceremony, but we think the unfortunate outfit she wore should have gotten her carded. The custom piece by Taylor Jean Cox was gorgeous in theory, with a plunging neckline and high slit skirt designed to flatter the gorgeous athlete's figure. However, it's hard to believe the piece was made especially for Morgan, considering how frumpy and ill-fitting the frilly metallic bodice seemed to be, bunching along her waist and creasing throughout the silver fringes. While not egregiously offensive, it was lacking the oomph anticipated on such a big night.
The devil was in the details for both Patrick and Brittany Mahomes' looks
Some couples bring out the best in each other, but unfortunately, Chiefs Quarterback Patrick Mahomes and his wife, Brittany, both showed up to the 2023 ESPYs in outfits that brought out their absolute worst. While the silhouette of Brittany's Versace dress was flattering, the pocket-style bra cups held together with backpack-looking release buckles completely cheapened the outfit. Patrick's look was just as tacky, with no shirt under his peach blazer and a pair of white-framed Oakley wraparound sunglasses. This two-for-one worst dressed is especially disappointing, as the typically stylish couple looked equally as confused regarding their outfit details.
Naomi Osaka's 2021 ESPYs look was a rare miss
Tennis pro Naomi Osaka is one of the leading authorities on fashionable sportswear in the 2020s. However, fashion is a learning process, and her 2021 ESPYs dress proves that you have to take the ups with the downs. The Louis Vuitton ambassador opted for one of the brand's Cruise collection pieces, but it was quite a questionable outfit. A zebra-print cape top embellished with gold roping gave the upper half of her body a shapeless silhouette, and tucking the middle of the top into a horizontally-pleated green leather skirt didn't improve things. Osaka may have won Best Female Athlete that year, but this was not her best look by a long shot.