The 2026 Kentucky Derby Was Full Of Fashion Flops

The Kentucky Derby returned in full swing, and just as the 2025 Kentucky Derby was a fashion nightmare, the May 2026 event brought no shortage of fashion flops. Celebs from far and wide turned up at Churchill Downs in Louisville, Kentucky, for the iconic 152nd "Run for the Roses," wearing their boldest and brightest fits. While some guests nailed their looks, others made a complete mess of their attempts. As a multi-day event, these looks span the 13th Unbridled Eve Kentucky Derby Gala that took place on May 1, 2026, and the Kentucky Derby itself on May 2.

Known for its extravagant headwear paired with pastel or vibrant spring dresses with floral designs, the Kentucky Derby is a theatrical, high-fashion tradition. Often dubbed the 'Met Gala of the South,' the event even comes with its own style guide, presenting the 2026 Derby fashion as a 'gallery of art' to honor the race's timeless traditions while embracing modern trends and cultural influences. Collaborating with style editor Zanna Roberts Rassi, alongside top fashion partners and milliners, the guide curates Derby Day looks to inspire outfits that are as intentional as they are unforgettable. Those who missed the style guide's intentions, however, didn't just fall short on trendy Derby fashion — they delivered full-blown style misfires that should have never left the starting gate.

Nicole Scherzinger can pull off almost any look, but she didn't quite do that here. After singing the national anthem at the Kentucky Oaks, the former Louisvillian stepped out on the Derby red carpet in a black-and-white polka dot dress paired with a black mesh hat with chiffon detailing. From her headwear down to her waist, the look showed promise. However, beyond that, it failed to deliver. Unfortunately, the bell-shaped hemline, which stopped just above her ankles, created an unflattering profile that weighed down the entire ensemble.

When Melissa Joan Hart showed up in a Michael Costello teal velvet halterneck dress with cutout details, she didn't consider how inappropriate it was to wear a dark velvet gown in the daytime, during spring.

Traditionally a winter fabric, velvet pairs best with formal after-dark occasions such as black-tie or holiday events. The dress reflected unevenly in the sunlight, looking patchy with inconsistent shading across the surface. Hart also wore a large fascinator crafted from thatched silver wires, topped with a flower and feather, which ultimately led to a discordant ensemble.

Perhaps if Gina Torres ditched her brown leather belt and swapped her straw hat for something more Derby-worthy, she could've elevated her casual white linen button-down dress. As it stood — with the addition of the brown leather boots and black satchel bag, adorned with a rose — the look felt underwhelming and unfortunately lacked the elegance the day demands, suggesting she made minimal effort for Derby Day. While some women opt for embellished takes on the gender-fluid hat, Torres' pared-back accessory felt uninspired for such a high-fashion event.

Legendary singer Chaka Khan was quite the sight at the Barnstable Brown Kentucky Derby Eve Gala. Dressed in a long-sleeved, floor-length bodycon dress completely covered in glittering embellishments, the 'Queen of Funk' shimmered as bright as a disco ball. 

While the dress may have dazzled at a nighttime party or club setting, it was a total miss for the Southern chicness of the Kentucky Derby. Known for her eccentric, larger-than-life fashion sense, we can't completely blame the "I'm Every Woman" singer for staying true to her signature style.

Patti LaBelle definitely delivered a show-stopping look at the Barnstable Brown Kentucky Derby Eve Gala red carpet. However, her satin, aqua, off-the-shoulder pantsuit with a train, paired with crystal jewels, leaned more into enchanted wedding-guest fashion than anything else.

The outfit's sheen and fluid texture felt better suited for an evening-time setting, though the "On My Own" singer clearly wears what she loves. LaBelle has, in fact, been spotted wearing her aqua pantsuit on more than one occasion.

If there's a way to overdo it at the Kentucky Derby, Star Jones did just that. While the TV personality embodied the Derby's classic, elaborate attire, wearing her wide-brimmed hat overflowing with feathers, flowers, leaves, and other elements, she went a step further by also adorning her hair with crystals and flowers.

Her matching periwinkle dress also made for quite a spectacle itself, with its soft chiffon layers and delicately placed feathers. She topped off the over-the-top look with a Kurt Geiger London Mini Brixton multi-colored rhinestone shoulder bag and Valentino Garavani VLogo slingback pumps.

Leslie Grace ditched the springtime Derby colors for a black-and-white ensemble at Churchill Downs red carpet (right). Though opting for visibly subdued shades, the "Conga" singer's tailored, lace blazer dress, complete with black ribbon ties, was a little too rigid. Nonetheless, she pushed the look further, pairing it with a lone black feather fascinator, leather gloves, and black stockings. Also attending the Unbridled Eve Kentucky Derby Gala (left), she maintained a color-reserved approach, wearing a too-formal black dress, completely void of a headpiece.

Spotted on the Churchill Downs red carpet, Chaka Khan decided on a monochromatic black ensemble that had way too much going on. The singer's look — a sheer top and ruffled, asymmetrical silk skirt with lace embroidery paired with an ornate Dolce & Gabbana belt, stockings, slouchy boots, and a saucer hat with mesh detailing, topped with oversized sunglasses — was a complete mess. The look was disorderly and borderline theatrical, making it one of the year's biggest fashion flops.

Former finalist on NBC's "The Voice", Lana Scott Beck was a standout celeb at the 2026 Kentucky Derby, performing at the "Oaks Survivors Parade", and even creating the Derby anthem, "Running For The Roses." Unfortunately, her red carpet 'fit didn't quite land.

Though the country singer fulfilled the tradition of a showy headpiece, her satin tie-dye, loose-fitting mini dress proved rather unflattering. Plunging deeper into the abyss of faux pas, she opted for white, slouchy cowboy boots, further throwing off an already-offbeat outfit.

NBC correspondent Andrea Canning had a few looks at the 2026 Kentucky Derby that missed the mark. For her red carpet appearance at Churchill Downs (left), the news anchor's relaxed white tie-blouse and handkerchief skirt clashed majorly against her peers' Derby fashion. Canning paired her outfit with a small, understated fascinator and casual heel, making this an underwhelming fashion miss. In another look (right), she wore a burgundy leather-look dress with cutout detailing. While bold, the piece was an unlikely choice for the event and was out of sync with the traditional aesthetic.