The Worst-Dressed Celebs At The 2025 Kentucky Derby

The Kentucky Derby is the one day of the year when we all become horse racing fans, even if we don't know a thoroughbred from a thoroughfare. It's yet another occasion for celebs and society folk to see and be seen, and in this case, the dress code is the fun part. As with major British equestrian events, the annual Run for the Roses is a garden-party extravaganza featuring spring colors, fun prints, and over-the-top headpieces to rival those seen at royal weddings. (It really is a pity we Americans don't wear fascinators more often.) The 2025 event was no exception. Despite the rainy weather, plenty of singers, actors, and other notables turned out at Churchill Downs in their best pastels, florals, polka dots, and oversized toppers to watch Sovereignty beat out the favorite horse, Journalism, in the 151st Derby.

Most of the attendees got the style memo and looked appropriately festive. However, there were a few misses along the way: mismatched pieces, poor pattern choices, and one couple who really stood out in the wrong way. These are the fashion flaws that we caught; do you think we picked the winning losers, or are we way back in the pack?

Among the pro sports figures attending the Kentucky Derby was Eric Wood, formerly a center with the Buffalo Bills. He and his wife, Leslie, are regulars at the race, so they really should have known how to pull together a cohesive look. Leslie's dress fabric was a hair too close to a grandma's couch fabric to be truly stylish, but her husband was the true cringey standout. Eric's blue plaid sports jacket, tan pants, and cowboy hat clashed both with one another and with Leslie's ensemble. He's rocked the plaid to much better effect in past years (as this Instagram post shows), so we hope to see an improvement in 2026.

Bonnie-Jill Laflin has had quite the career trajectory. Formerly a cheerleader for the Cowboys and 49ers, she's now the first-ever female scout for the NBA, as well as a frequent TV and podcast host. Laflin even shares something with Meghan Markle: Both opened the famous briefcases on "Deal or No Deal" (though not, alas, in the same season). The ensemble she chose for the Derby would have been a clear winner if not for that one odd detail. The bow, with its trailing tail, adds nothing to the design; on the contrary, it interrupts the clean line of the dress and distracts from what should have been the star of the show: Laflin's spectacular hat.

Hotelier and art connoisseur Steve Wilson is another Derby regular who doesn't play it safe when it comes to fashion. In 2017, he told the Courier-Journal, "Black tie doesn't mean black tie for me. ... I feel like the success of [his 21c Museum Hotels] gives me the opportunity to be expressive and carry that contemporary art to a new level, even in what I choose to wear." Expressive is the word for his getup this time, though we're not sure exactly what he was trying to express. He paired silver pants with a straitjacket-esque coat featuring a bison. It would have looked just fine at an Albuquerque or Tulsa event, but Louisville is horse country all the way. The tone was also far too drab for the Derby, where brighter is always better. If that bison had been cobalt blue or cherry red, that might have been a different story.

Discovered on "The Voice," country-pop singer Lana Scott had the honor of performing at the 2024 Kentucky Oaks, the race traditionally held the day before the Derby. She returned to Churchill Downs this year as a guest, opting for an upscale cowgirl-ish look that didn't quite hit the mark. Scott's pearl-studded Western minidress and white boots clashed with her ladylike gloves and garden party hat. And that fuzzy pink clutch belonged with another fashion aesthetic altogether. We'll give Scott a pass this time since she's just starting out. But if she proves to be the country superstar her peers are predicting her to be, she'll need to step up her wardrobe game for future red carpet events.

Amber Brkich Mariano and "Boston" Rob Mariano are legendary to "Survivor" fans. Not only did Brkich win Season 8 of "Survivor: All-Stars," but she and Mariano fell in love along the way. (If you can spend a month together on a remote island enduring the elements and a diet of rice without going crazy, you know it's romance.) They've been married since 2005 and are the proud parents of three daughters. Unfortunately, their outfits for the occasion looked more like they were headed back to the South Seas than to a high society horse race. 

First, the good news: We're in love with Star Jones's Derby hat. It's both flattering and just over-the-top enough without being ridiculous. We just wish the rest of her outfit was as fabulous. The attorney and former co-host of "The View" picked a marabou-trimmed minidress that comes dangerously close to looking like the inappropriate outfits Kimberly Guilfoyle has worn. More to the point, it just doesn't match the headgear well enough. A floaty chiffon number in a pale blue or lavender would have been far more complimentary.

The biggest losers at the 2025 Kentucky Derby were Jayson Werth and his wife, Julia. Werth, a former MLB player, came to cheer on Flying Mohawk, the Derby racer he owns. Not only did Flying Mohawk finish a dismal 12th, but the Werths' garish green outfits made them the laughingstock of the whole afternoon. We personally believe they came to Churchill Downs right after a fan fest of "Wicked," but some social media users had other ideas. Many comparisons to Willy Wonka and his famous candy factory were posted. Fox Sports analyst Jared Smith had another thought. He chuckled on X (formerly Twitter), "Jayson Werth: Kentucky Derby by day, terrorizing Gotham by night."

Jayson Werth
Kentucky Derby by day
Terrorizing Gotham by night pic.twitter.com/qdAuhYtjsg

— Jared Smith (@jaredsmithbets) May 3, 2025

Batman doesn't normally go after fashion crimes, but in this case, he might want to make an exception.