The Worst-Dressed Stars At The 2026 Kentucky Derby

The weather was clear, the mint juleps were flowing, and the mood was upbeat at the 2026 Kentucky Derby. The 152nd annual Run for the Roses made history on May 2 when Golden Tempo beat out his competitors at Churchill Downs, making Cherie DeVaux the first female trainer to win the Derby and only the second to train a Triple Crown winner. (Golden Tempo was a 23-1 long shot, so anyone who wagered big money on him came away quite happy themselves.)

Like all prestigious events, the Derby is known for welcoming celebrities from the entertainment and sports worlds who come dressed in their best. In this case, that means a semi-formal ensemble, preferably in spring pastel colors, and for the women, an elaborate hat or fascinator to complete the look. It's basically the American version of the looks one sees at the Royal Ascot race. Yet just as the royals themselves have made fashion missteps over the years, so too do the stars who turn up in Louisville every May.

This year, attendees would have done well to take their cues from Dylan Dreyer's Kentucky Derby outfit, a floral number with a matching hat that was just fun enough to be appropriate without veering into utter absurdity. Some, in fact, did strike that balance. Others, on the other hand, could have used some expert advice on color and style (or, perhaps, a good tailoring job) before stepping out of their hotel room. We chose just a few of the more egregious examples for your viewing pleasure, and we're keeping our fingers crossed that next year will see more hits than misses. 

Neil Patrick Harris and his husband, David Burtka, have one of the longer-running marriages by Hollywood standards, so one might assume they're good at giving each other advice when it comes time to choose an outfit for a big event. Apparently it isn't so. How else to explain the ill-fitting jackets, the eye-catching patterns, and Burtka's Bermuda shorts and knee socks? Perhaps "A Series of Unfortunate Events" led to this fashion disaster. Or maybe, knowing their love of fun and whimsy, they deliberately selected their clothes for maximum wince effect.

The iconic Chaka Khan ("I'm Every Woman") is still wowing audiences after more than half a century. She paused her busy touring schedule to join the crowds at Churchill Downs, but it looks like she missed the memo about the traditional color scheme. Instead of choosing something floral or pastel, Khan dressed in head-to-toe black as if she were headed to a funeral instead of a horse race. Even her hat was far more subtle than most.

Lana Scott Beck was one of the worst-dressed celebs at the 2025 Kentucky Derby (in our opinion, at least), but we were willing to overlook her fashion foibles at the time. As a winner of "The Voice" who was just launching her country career, Beck seemed to be figuring out her personal style. Now, a year later, it looks like she's sticking to her Derby aesthetic of minidresses, white cowgirl boots, and a matching fuzzy purse. It didn't work last year, and it doesn't fare much better now.

Influencer Bridget Bahl, founder of The Bar fashion brand, would have had a winner with her nature-inspired choice if it had been a better fit. The slim fit of the slip dress was so unforgiving that it pulled across her midsection in an unflattering way. Her oversized hat could also have used just a touch less tulle and a narrower brim. (Could she actually see the horses on the track without pushing the topper up?)

Backstreet's back, but it's not quite all right. Howie Dorough of the Backstreet Boys turned up in Louisville with his wife, Leigh Anne Dorough. After years of thrilling fans in flannels, denim, and sharp white suits, it was jarring to see Dorough in a mismatched ensemble of a navy jacket, purple pants, and brown loafers. The hat didn't help. Leigh Anne's form-fitting dress with flapper fringe was a better match, but still nothing to write home about.

Performing the National Anthem at the 2026 Kentucky Derby must have been a huge bucket list item for Derek Trucks and Susan Tedeschi of the Grammy-winning Tedeschi Trucks Band. Sadly, the married musicians' Derby outfits wouldn't win any awards. Trucks' blue plaid jacket and cowboy boots were fine, but adding a vest broke up the total look. As for Tedeschi, her black spangled minidress and dark hose were more appropriate for an evening event, and they clashed with her springlike, flowered hat.

As the mayor of the Derby's home of Louisville, Craig Greenberg, should have led the pack, fashion-wise, on the city's biggest day. Sadly, he didn't. His lavender suit was appropriate as far as color goes, but the baggy fit was way off, and his sneakers were far too casual. His wife, Rachel, didn't fare any better. Her frumpy drop-waist dress with short puffed sleeves gave total '80s vibes; with some lace, it would have been classic Gunne Sax. At least she committed completely to the look by pairing it with espadrilles.