Hats and fasteners and jewels, oh my! The stars came out in full force for the 152nd Kentucky Derby, looking dapper and dashing as they walked the red carpet on May 2, 2026. The annual event is not just about the legendary two-minute horse race, but about the classic and colorful fashions on display at pre-parties and the race itself.
According to the Kentucky Derby Style Guide, Derby Day at Churchill Downs is “an exhibition where fashion and art meet in the form of color, textures, and silhouettes.” 2026 Guest Style Editor Zanna Roberts Rossi wrote that she couldn’t wait to see everything “from richly pigmented hues to beloved soft springtime pastels, fit-and-flare waists, and of course, the beautiful fascinators and headwear that add its signature Derby flair to every outfit.”
Celebrities from sports and entertainment flocked to the event hours before the race to flaunt their fashions and sip on mint juleps. Here are some of our favorite star sightings and colorful ensembles.
Hats Off to the Stars Who Topped Off Their Looks With Fabulous Fascinators & Handsome Hats
GettyCassandra Johnson, wife of former NBA star Avery Johnson, is a staple at the Kentucky Derby, and she definitely stood out on the red carpet with her floral crown and coordinated silk dress.
In the 2026 Style Guide, Rossi advised guests to think of “the HAT as the focal point of your canvas” when devising their looks. For women, she said that could include a “minimalist” pillbox cap, feathers or florals (like Johnson’s crown), or a skull cap or wide-brimmed hat adorned with ribbons and jewels.
GettyMelissa Joan Hart and Danica McKellar, who both rose to fame on 90s sitcoms (“Sabrina the Teenage Witch” for Hart and “The Wonder Years” for McKellar) attended the Derby together, both sporting sleeveless dresses with coordinating hats.
Olympian Lolo Jones dazzled in an ornate Alexander McQueen gown with a whimsical fastener to top off her look. She told Yahoo Sports that the fascinator was designed by a local Louisville artist who gave her “a whole demo” so she could put it on herself for Derby Day.
GettyTV personality Star Jones took the assignment to new heights, with a wide-brimmed hat piled with blue feathers and florals. She also had florals and jewels cascading down her hair. Singer and “In The Heights” actress Leslie Grace, who released a new album on the day before the Derby, went with a simple but elegant black feather fascinator to coordinate with her white lace dress.
GettyAlso looking fabulous were music icon Chaka Khan, who performed the previous night with Patti LaBelle at a Derby pre-party; Nicole Scherzinger, who performed the national anthem earlier in the day, and “Dateline NBC” correspondent Andrea Canning.
GettyBut it wasn’t just the women who dove headfirst into Derby Day. There were plenty of guys wearing dapper hats, too, including *NSYNC’s Joey Fatone and former Bon Jovi guitarist Richie Sambora.
Cutest Celebrity Couples at the 2026 Kentucky Derby
GettyNumerous coordinated couples graced the red carpet on Derby Day, too. Actor Neil Patrick Harris and his husband, David Burtka, wore wonderfully whimsical outfits. Harris sported a black suit coat adorned with embroidered feathers, while Burtka coordinated a garden-themed suit coat with matching shorts, knee-high socks, and a quaint bow tie.
GettyAlso in attendance were *NSYNC’s Lance Bass with his husband, Michael Turchin, both dressed smartly in spring suits, and famed Latin music sensation Luis Fonsi and Águeda López, who coordinated their black-and-white outfits.
GettyMeanwhile, onscreen couple Andrew Walker and Odette Annable also walked the red carpet. The duo stars in “Kentucky Roses,” a new Hallmark Channel movie filmed at Churchill Downs that premieres on the network hours after the race, at 8 p.m. Eastern time.
