The Worst-Dressed Celebs At The 2026 Kentucky Derby

If you thought dressing up for horse races was a more contemporary notion, let us deliver a fun little fashion history lesson: Since the early 20th century, ladies (and gentlemen) have considered horse races an opportunity to strut their style stuff, perpetuating the idea of statement race-day fashion. While hats were likely worn to protect oneself from the sun, the tradition has continued, with creative toppers dominating headwear and creating the base of the outfit. And the 2026 Kentucky Derby did not disappoint in the hat arena, with milliners' magnificence making a strong showing.

Just as there were the best and worst-dressed celebs at the 2025 Kentucky Derby, bold-faced names delivered hits and misses this year as well. Among many misses were looks that felt inappropriate for the daytime event and struggled with the cooler-than-usual weather which sat in the high 50s. The Kentucky Derby itself put out a style guide for fans hitting Churchill Downs: "Women typically wear bold, stylish outfits centered around statement hats. Think pastel dresses, peplum styles, and elegant accessories. Comfortable yet chic shoes like wedges or flats are a must ..." Pour yourself a mint julep and see how Derby-goers like Chaka Khan and Melissa Joan Heart didn't make it down the home stretch, fashion-wise.

For the 2026 Kentucky Derby, queen of funk Chaka Khan looked like she'd gone to the opening night of "The Devil Wears Prada 2" and decided she'd re-wear the outfit the next day to Churchill Downs. Aside from the on-point hat, the all-black outfit with the dominant Dolce & Gabbana belt and other leather accessories did not fit the Derby's own brief. It also didn't feel very "springtime pretty," which is what many attendees usually channel.

Perhaps the "Clarissa Explains It All" actor can explain what happened here. For the 152nd running of the Kentucky Derby, Melissa Joan Hart opted for a crushed velvet floor-length gown that didn't feel daytime-appropriate, especially with the torso cut-out. It also didn't coordinate terribly well with the hat, which looked to be silver wire for the brim, topped with a white flower with some sort of metal accent in the center. Picking a hat and dress that at least matched would've helped send this muddled mess in the right direction.

Star Jones has landed on more than a few worst-outfit lists over the years, including the worst-dressed celebs at Melania and Donald Trump's 2005 wedding. And we welcome the former "The View" cohost back again. This time, Jones looked like she was channeling her 8-year-old self playing race-day dress up as a kid. The flowers dangling in the hair along with the poofy ice-blue dress didn't work on someone in their 60s. Overall, the 'fit lacked a sophistication we'd expect from this lawyer and TV personality.

Country singer Lana Scott Beck looked like she pinned pics of Princesses Beatrice and Eugenie at the Royal Ascot for her 2026 Kentucky Derby inspiration. We won't be repinning this look, however. The watercolor print on her dress is pretty, but the accessories were a deal-breaker. The furry turquoise purse sparred with the hat, and then there was the cowboy boots ... Why do country singers (and politicians!) feel the need to wear cowboy boots like it's a badge of honor? This footwear ultimately let the look down.

Influencer Lauren Gibson posted pics to her Instagram of her at the Kentucky Derby in a pink gingham dress, with pink and pearl accessories and jewelry to coordinate. This look felt perfect for watching the races. However, a second outfit didn't deliver on the brief as well. The black coat brought down the rest of the summery pieces with its heavy feel. We also would've preferred a hat that didn't sit so low on the forehead, obscuring half her face. This look was on its way, but didn't make it to the finish line.

Actor and social media influencer Michelle Kennelly looked lovely in a date-night outfit that's perfect for fall, not for the daytime springtime races. No, not every attendee needs to be in pastels or floral-print dresses, but little touches can make all the difference. For example, the microbag she carried is one of the outdated handbag trends to ditch for summer 2026, and the black tights felt too heavy for what should've been an easy-breezy daytime 'fit. 

Stunning singer and actor Leslie Grace looks like she was one of the Kentucky Derby attendees who struggled with the cooler-than-normal temperatures at this year's races. Her black-and-white outfit is chic, but would look more appropriate for the Rockefeller Center Christmas Tree Lighting Ceremony, rather than the Derby. The black leather gloves feel more apropos for Manhattan in December as opposed to springtime in the South.