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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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.
Bill Belichick
North Carolina head coach Bill Belichick and his girlfriend, Jordon Hudson, made the trip to Churchill Downs together.
Belichick and Hudson actually underwent an outfit change before hitting the red carpet.
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.
Nate Burleson
Former NFL wide receiver and current CBS analyst Nate Burleson put a lot of thought into his Kentucky Derby appearance.
Rob Gronkowski
Former NFL tight end Rob Gronkowski is no stranger to the Kentucky Derby, as he is a frequent attendee at Churchill Downs.
Von Miller
Super Bowl 50 MVP Von Miller brought out a baby blue jacket and pants for the Kentucky Derby red carpet.
Maggie Huber/Special to Courier Journal/Imagn Images
Sue Bird
WNBA legend Sue Bird is wearing an all-white outfit as she attends the Kentucky Derby today.
Warren Moon
NFL hall-of-famer Warren Moon's outfit on the red carpet includes a checkered jacket with a green tie and a tan hat.
Maggie Huber/Special to Courier Journal/Imagn Images
