Kentucky Derby live outfits tracker: Best and worst dressed from the sports world, including Bill Belichick and Jaxson Dart

While the Kentucky Derby marks the official beginning of Triple Crown season, it has also become a destination event for celebrities.

For some, the Kentucky Derby is one of the most important horse-races of the year, with one horse etching its name into history. However, for others, the Derby is one of many iconic sporting events to attend with a specific outfit in mind.

The lead-up to the race is the time for those attending to show off their fashion senses with standout outfits. Of course, a huge part of Kentucky Derby outfits are the hats, as fans get the chance to wear their most extravagant piece of headwear on the red carpet.

The race itself only last a few minutes, but the event takes place over the course of an entire afternoon at Churchill Downs. Many athletes who have the time tend to descend upon Louisville to witness "The Run for the Roses" in person.

With that in mind, The Sporting News is tracking the best and worst outfits from the sports world during the 152nd Kentucky Derby.

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• How much money will winner of this year's Kentucky Derby receive?

Best and worst 2026 Kentucky Derby outfits

Jaxson Dart

New York Giants quarterback Jaxson Dart is on hand for the Kentucky Derby after a successful rookie season in 2025.

Jaxson Dart just threw a lil something together for his appearance at the Kentucky Derby 😎 pic.twitter.com/iX854eNFvu

— Yahoo Sports (@YahooSports) May 2, 2026

Bill Belichick

North Carolina head coach Bill Belichick and his girlfriend, Jordon Hudson, made the trip to Churchill Downs together.

Bill Belichick and Jordon Hudson pull up to the Kentucky Derby 🏇 🐐 pic.twitter.com/xmFc8p5Xn2

— Yahoo Sports (@YahooSports) May 2, 2026

Wan'Dale Robinson

Tennessee Titans wide receiver and former Kentucky Wildcat Wan'Dale Robinson returns to Kentucky after getting a big deal in the offseason.

Wandale Robinson looking sharp here at the Kentucky Derby!! pic.twitter.com/OPSs5L7Ljw

— Mario A Maitland (@MarioMaitland_3) May 2, 2026