The Kentucky Derby isn’t just about horses…it’s basically a celebrity runway with mint juleps, wild hats, and A-list madness. Every year, famous stars pull up in their best fits, place their bets, and fully lean into the vibes.
With this year’s Derby set for May 2, 2026, the hype is already building. And if history tells us anything, we’re about to get another round of viral moments, unexpected wins, and outfits we’ll be talking about for weeks.
So before the chaos kicks off again, let’s rewind and relive some of the biggest celeb moments—from iconic looks to headline-making drama—that completely stole the show.
1. Shaboozey
Shaboozey understood the assignment in 2025. The country star pulled up in a peach-toned three-piece suit, finished off with a cactus bolo tie—very Derby and very extra, in the best way.
According to Rolling Stone, he arrived early enough to actually enjoy the races before the big moment, casually making his way around the track with a cigar in hand, stopping to chat with fans and mingle with horse owners.
Later, he retreated to the ultra-exclusive Woodford Reserve Paddock Club, aka one of the most exclusive spots at the Derby. Think premium views of the paddock, dedicated service, and a wine and bourbon selection that doesn’t miss on luxury.
2. Jack Harlow
Jack Harlow might be a Derby regular at this point, but he still knows how to keep things interesting. Last year, he kept it more low-key compared to his past headline-making moments—yes, including that iconic Churchill Downs era with Drake.
Instead, he kicked back in the Turf Suites with his circle, soaking in the atmosphere, snapping photos with fans, and enjoying the day without making it a whole production. But don’t get it twisted, the energy picked up later. Harlow hosted an after-party in downtown Louisville where he jumped behind the DJ booth and started spinning hits.
3. Alix Earle & Braxton Berrios
This pair didn’t just attend the Derby in 2025…they accidentally became the plot. Before the race even started, Braxton Berrios made a totally random pick, pulling the name “Sovereignty” out of a hat on the red carpet. And somehow… he nailed it.
Sovereignty went on to win at 7-1 odds, beating the favorite Journalism. Watching it all go down, Berrios—standing next to Alix Earle and Josh Richards—literally climbed onto a chair to celebrate as the crowd went wild, according to Rolling Stone.
Moments like this prove how unpredictable the Derby can be. According to early odds, like those seen on TwinSpires.com, “Paladin” is emerging as the early favorite, so it will be interesting to see if Alix Earle and Braxton Berrios can call it right again.
4. Stephen Wilson Jr.
Not every standout moment comes from the main stage. Stephen Wilson Jr. quietly stole some attention last year as a surprise opener at one of the Derby weekend parties.
Performing at Old Forester’s Paristown Hall, he warmed up the crowd before the bigger acts took over. Early in his set, he made sure to highlight where he came from, repping Seymour, Indiana—a small but meaningful nod, especially given its proximity to Louisville.
5. Travis Kelce
Travis Kelce didn’t just attend the Derby…he fully converted. Talking about the experience on his podcast with Jason Kelce in 2024, Taylor Swift’s fiancé made it clear he’s already planning a return: “I’m a Derby guy now, man. It was so much fun.”
And he doubled down with: “It was a once-in-a-lifetime experience that I am definitely going to try and experience again. It was fun just being part of the entire environment.”
Kelce leaned all the way in style-wise too, showing up in a clean off-white pinstripe suit, topped with a fedora featuring a blue feather—fully embracing the Derby’s over-the-top fashion culture.
6. Simone Biles
When Simone Biles shows up, the internet will talk. And that’s exactly what happened in 2025.
She attended alongside her husband, Jonathan Owens, and the coordinated looks alone were enough to get social media talking. Biles went for a lavender strapless dress paired with a dramatic feathered hat, while Owens matched the color palette with his own tailored look.
Fashion-wise, the internet was mostly in agreement: they nailed it. The conversation shifted, though, when Biles delivered the traditional “riders up” call before the race: “Ladies and gentlemen, the city of Louisville, the Commonwealth of Kentucky and sports fans from around the world have been waiting for this moment,” she said before leaning forward, adding “riders up” and blowing a kiss to the crowd.
Some fans loved the passion and energy she brought. Others… not so much, calling it “cringey” and “ridiculous.” Either way, she had everyone talking…which is kind of the whole point.
At this point, the Kentucky Derby is just as much about celebrity moments as it is about horse racing. Between bold fashion, unexpected wins, and viral soundbites, it’s basically the Met Gala of sports…with way more betting and bourbon.
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