The Worst-Dressed Stars At The 2025 Kentucky Derby
The celebs who attended The Kentucky Derby 2025 likely dropped wads of cash to bet on their favorite horses and used whatever money they had left to fund their most daring, photo-ready looks for the fabulously glitzy event. At least, that's what was supposed to have happened. While many celebrities — such as actor Selma Blair, who donned a gorgeous yellow number — effortlessly wove southern charm and glamour together for their Derby looks, just as many, it seems, dropped the ball.
In case you didn't know, the Kentucky Derby lays out its general fashion guidelines each year, tweaking them slightly to account for ever-changing trends. According to journalist Zanna Roberts Rassi, who helped curate the vision on the event's website, choosing bold colors and striking shapes would push attendees toward their perfect Derby look, but even those qualities came second to the most important component of the look: the hat. In Rassi's opinion, guests should actually find the perfect hat first, then find a look that complements it. Makes sense! She also advised guests to, among other things, embrace a spring-friendly color palette. But not everyone followed the rules!
Lana Scott's look didn't come together
Country singer Lana Scott's vocals soared as she performed the National Anthem at the Kentucky Derby, but her outfit barely made a splat. The songstress donned a periwinkle blue blazer-type dress adorned with what appeared to be pearl appliques. She paired the daring number with white, knee-high boots, matching gloves, and a poofy, pink clutch, leading one to wonder exactly what her original color scheme was. The upside to the look is the fact that her asymmetrical white hat, set off by her fiery red hair, worked overtime to draw the eye from the distracting outfit (but only a little).
Tianna Roblliard dressed for the wrong event
Influencer Tianna Roblliard attended the Kentucky Derby, but she certainly didn't dress for the upscale event. While the popular content creator picked a cool white hat adorned with green flowers to cap off her look, the rest of her outfit left much to be desired. As in — it didn't fit any of the expected themes. The two-piece green number looked perfectly suitable for a day out on the town or even, dare we say, after-workout attire, but for the Derby, we expected more.
Alix Earle was underdressed
Alix Earle is another influencer who scored a spot among the raucous Derby crowds. However, her outfit did little to mimic the exuberant energy of the races. Earle instead went with an all-black dress with a plunging neckline that stopped at her mid-calf. She paired the look with a matching black hat positioned halfway off her head. We don't want to say that the look probably would've worked better for the homegoing service of, like, a fashion designer or a 1940s-era actor, but she didn't really give us many options here. Add this look to the list of Earle's weird fashion moments.
Chris Tucker's Derby outfit was too plain
Actor Chris Tucker also attended the Kentucky Derby. Though his enthusiasm for the horse-racing event was definitely felt in his Instagram caption, which read "The Kentucky Derby Baby!!" alongside his outfit of choice, the look didn't command nearly as much hype. Unfortunately, Tucker's black, double-breasted suit did little to evoke the high fashion these long-standing races are known for. And while the silver tassels over his right shoulder added a touch of pizazz to the look, he would've better blended in at, say, an award show.
Cassandra Johnson's look was way over the top
Cassandra Johnson, the wife of NBA alum Avery Johnson, definitely went all out for her Kentucky Derby look, but in this case, that was not a positive. The gorgeous WAG showed up to the event wearing a dizzying pink, orange, and yellow two-piece skirt set that she offset with matching shoes and a similarly colored Christian Dior handbag. Had she stopped there, it would've been fine, but she topped off the look with a monstrous bouquet of colorful flowers, which stood in for her headgear. Individually, each piece may have worked, but together, it was overly stimulating to the eye.
If these Derby fashion disasters left you curious about more questionable style moments, don't worry — we've got you covered. From fashion faux pas at Coachella 2025 to baffling blunders at this year's White House Correspondents' Dinner, the chaos didn't stop at Churchill Downs.