Every year, the Kentucky Derby turns Louisville into a display of style, tradition, and turf. While the race is the headliner, the fashion show is what the majority of eyes are really on. It’s a mix of Southern belle, springtime chic, and high-society weirdness. But even with months to plan and stylists by their side, not all celebrities scored. The 2025 Kentucky Derby had some just plain baffling fashion decisions that left onlookers scratching their heads, did they get dressed in the dark?
Here’s a closer examination of the celebrities who made people turn heads for all the wrong reasons.
The Werth’s Go Green – Literally
Jayson Werth, ex-MLB player, arrived prepared to root on his horse, Flying Mohawk, who unfortunately didn’t deliver on the track. However, it wasn’t only the lackluster effort on the track that made headlines. Werth and his wife Julia arrived in coordinating green apparel so garish and theatrical, they seemed better placed at a Broadway costume call than Churchill Downs. Social media buzzed with comparisons, from Willy Wonka’s factory workers to comic book villains. Sports commentator Jared Smith even joked on X (formerly Twitter) that Werth was working second shift as Gotham’s new arch-villain.
Eric Wood’s Style Fumble
Ex-Buffalo Bills centre Eric Wood could have stayed in the locker room and stuck with it. His attire, a discordant combination of tan pants, blue plaid shirt, and cowboy hat, conflicted not just with itself but with wife Leslie’s couch-print dress. With the couple’s Derby attendance history, one would expect more harmony. Wood has dressed in plaid more successfully in past years, as documented on his Instagram, so this year’s ensemble is all the more baffling.
Bonnie-Jill Laflin’s Misplaced Bow
Renowned for shattering barriers in the NBA and illuminating TV screens on “Deal or No Deal,” Bonnie-Jill Laflin typically aced her public outings. Her 2025 Derby ensemble had promise, sophisticated hat, streamlined silhouette, until a huge, sagging bow ruined the whole look. Rather than bringing panache, it was an unwelcome focal point that took attention away from an otherwise elegant outfit.
Lana Scott’s Style Identity Crisis
Country-pop singer Lana Scott, a fan favourite from “The Voice,” attempted to merge Nashville charm with Derby sophistication. The outcome? Baffling. Her pearl-studded minidress were practically yelling saloon, while gloves and flowers on her hat were softly saying garden party. Add in a fluffy pink clutch, and the entire ensemble resembled three disparate Pinterest boards crashing into one another. As a rising star, she has time to get her red-carpet game down, and we implore she does.
Steve Wilson’s Artistic Misfire
Hotel tycoon and art collector Steve Wilson has a reputation for wearing his personality on his sleeve, literally. But his 2025 look, with its bison-patterned coat and metallic pants, was more befitting a quirky Santa Fe gallery opening than the bright grass of Churchill Downs. Although creative expression is to be encouraged, Derby fashion requires color and coherence. Wilson’s subdued colors lacked luster in the face of pastels and flowers.
Star Jones’s Dress Let Her Hat Down
Star Jones’s hat was the Derby deserves: bold, chic, and photo-worthy. The marabou-trimmed minidress that accompanied it, however, did not step up to the plate. That the dress seemed disconnected from the headpiece is what left her looking incomplete. In a soft, flowing dress in lavender or sky blue, she might have had one of the day’s standout looks.
Survivor Style Gone South
Reality TV royalty Rob and Amber Mariano may have endured tribal councils and foreign jungles, but the fashion scene at Churchill Downs was more than they could handle. Their ensembles were more befitting a beach party than one of America’s most fashionable sporting events. Sometimes, nostalgia just doesn’t work when it comes to high fashion.
The Kentucky Derby is a celebration of heritage, horses, and headgear, and it provides the ideal opportunity for celebs to express their personality via fashion. But as these stars demonstrated, not all daring decisions result in triumph. For every stunning hat and sleek pastel, there’s always someone who goes off course. Here’s hoping next year’s mistakes are fewer, and the photo opportunities are even more spectacular.
Also read: Behind the Laugh Track: How the Cast of Modern Family Cashed in Sitcom Stardom
