The 2026 Kentucky Derby is underway, which means the horses are raring to go at the starting gate—and celebrities are out mingling in their finest spring-inspired threads at Churchill Downs.
Long established as a high-society affair showcasing the most elegant and extravagant styles of the era, the Kentucky Derby is entering its 152nd year, and with the new season comes fresh fits. The big hats. The vibrant pastels. The ruffled dresses and dapper suits. As spectators gather to watch the most exciting two minutes in sports at the race track, let’s take a look at the best-dressed celebrities and athletes attending the Kentucky’s most prestigious horse racing event.
Among the sports celebrities walking around Louisville, North Carolina coach Bill Belichick was seen with his girlfriend Jordon Hudson. Hudson posted a photo of the two of them holding hands while walking on the dirt track at the Kentucky Oaks race, the sister event to the Derby. “Not the first time we’ve trudged through the mud together,” she wrote in the caption.
Belichick was wearing a black suit while Hudson sported a black dress.
Bill Belichick and Jordon Hudson walk the #KentuckyDerby red carpet pic.twitter.com/4iS7fG1PB6
— Sports Illustrated (@SInow) May 2, 2026
Later, Belichick and Hudson walked the red carpet at the Derby, and they changed into more straightforward formal wear: a black suit and black dress, respectively.
Bill Belichick and Jordon Hudson walk the #KentuckyDerby red carpet pic.twitter.com/4iS7fG1PB6
— Sports Illustrated (@SInow) May 2, 2026
Giants quarterback Jaxson Dart strutted across the red carpet, too. He attended the Derby with his girlfriend Marissa Ayers, and he was decked out in a white striped suit complete with a white fedora. Real NYC mobster vibes:
.@JaxsonDart and Marissa Ayers break down their #KentuckyDerby fits 🔥 pic.twitter.com/UdArhFI1u8
— Sports Illustrated (@SInow) May 2, 2026
Patriots legend Rob Gronkowski made an appearance in a more subdued suit: a dark blue blazer and light chinos. He was showing off some cash in the inside of his jacket, being the high roller he is:
Rob Gronkowski pulls up to the Kentucky Derby ready to spend 💰 pic.twitter.com/qiK8Q0D2ek
— Yahoo Sports (@YahooSports) May 2, 2026
Here was CBS analyst Nate Burleson’s bold look on the red carpet—it’s one of the more modern Derby-inspired fits out there. Burleson chose to go down the polarizing short suit route, wearing a mint green-striped blazer with rose details paired with matching shorts.
What would you rate @nateburleson’s Kentucky Derby outfit 1-10? 😆 pic.twitter.com/alWxPlmg1x
— Yahoo Sports (@YahooSports) May 2, 2026
Spurs legend Avery Johnson threw together a blue suit on top of a light blue dress shirt, and he spoke a bit about San Antonio’s ongoing run in the NBA playoffs. Victor Wembanyama and co. rolled over the Trail Blazers in the first round and will face off against the Timberwolves next.
Spurs legend Avery Johnson on Victor Wembanyama and San Antonio so far in the playoffs 🗣️ pic.twitter.com/Niwga3GyoV
— Yahoo Sports (@YahooSports) May 2, 2026
NFL free agent Von Miller was also at Churchill Downs rocking a classy blue plaid suit and a matching hat:
Von Miller—why does he look…saggy? pic.twitter.com/gBDnsiNQjk
— jessica 🌵🪨✨ (@jess_felts) May 2, 2026
WNBA icon Sue Bird looked stunning in her fresh white fit, picking a neutral palette that truly goes with everything. Bird and her former partner, USWNT legend Megan Rapinoe, recently broke up after nearly a decade together.
Sue Bird in her Derby day fit! 🔥
— WNBA on NBC and Peacock (@WNBAonNBC) May 2, 2026
📺: The 152nd Kentucky Derby on NBC and Peacock pic.twitter.com/lIjRpwCYXE
Former NBA center Joakim Noah was probably the only one at the Derby who wore a leather jacket. On top of an NBA hoodie. We think it works? But members of the fashion police would probably stick up their noses at this fit:
“Yesterday I was on a camel in Morocco and today I’m at the horse races.”
— Talia Baia (@taliaontv) May 2, 2026
- Joakim Noah 🤣 (legend) pic.twitter.com/XA1EsQSEiw
As for some celebrity fashion outside of the sports world, Neil Patrick Harris looked very dapper standing alongside his husband David Burtka:
And here’s a video of some of the most over-the-top hats at the Kentucky Derby, because it’s not a Derby without the iconic headwear:
Churchill Downs turned into a runway 📸 pic.twitter.com/zc5pPZDW5b
— Yahoo Sports (@YahooSports) May 2, 2026
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This article was originally published on www.si.com as Kentucky Derby 2026: Bill Belichick and the Best-Dressed Celebrities at Churchill Downs.
