The Kentucky Derby is known as The Greatest Two Minutes in Sport, but is also now the largest fashion event in American Sports, recognized for wonderfully bold sartorial fashion. The annual event has become defined by vibrant colors, bold patterns, and dramatic hats or fascinators, and why not – when else does one get the opportunity to wear a truly over-the-top hat or fit?
“The original idea to create a day where attendees could wear their finest and enjoy a day in the sun at the track started in 1875 and continues to this day,” says Christine A. Moore, featured milliner of the Kentucky Derby since 2018, and who creates approximately 1,000 hats a year.
Americans were influenced by the formal European horse races across the early decades, with the Derby functioning as both a sporting event and an elite social occasion. But the fashion history for the event evolved at the same time as race day, and by the 1920s and 1930, guests had begun to cultivate their own fashions and traditions.
“Sporting events have become cultural events, and attendees have dress codes,” says Amy Grammer, a designer and Milliner, who has designed over 400 hats for the Derby, including for Jamie Hernandez, the wife of race-winning jockey Brian Hernandez. “Over time, as certain sports events gain popularity, a character-dress style evolves.”
Style is now an integral part of sports – think of the garden party style at Wimbledon, the sharp athleisure seen courtside at NBA games, or how Taylor Swift changed the culture of NFL fashion forever.
© Getty ImagesHats, in particular, are one of the most recognizable parts of the Derby – and often considered the main event – but this evolution also gradually happened over the decades.
“When the Derby was founded, hats were standard everyday fashion for women and signaled status and respectability,” says Brittany Cobb, founder of Flea Style and the creator of The Original Hat Bar, an experiential retail concept. “They started much more modest and refined; today, women go all out with their hat styles.”
© Polly SingerPolly Singer is one of the most well-known milliners for the Derby, making hats for over 20 years and designing thousands for the Kentucky Derby. The process begins after January 1 and doesn’t stop until hours before the big day, while the milliners are also working other events; Polly is also designing 16 hats for a group sitting in the Royal Enclosure at Royal Ascot on Ladies Day.
Polly credits the royal wedding of Princess Catherine and Prince William as bringing a modern twist to the Derby, with fascinators, saucer hats, and sculptural twists becoming more popular in the last decade.
In 2025 alone, spotted hats were 3 feet wide, had floor-length fringe hats, whimsical lego scenes of race events on the brim, and showgirl-style plumes of feathers
“The wildest design I ever did was a fascinator made from real horseshoes,” shared Polly, revealing it took weeks of small adjustments to get it to work. “It was a challenge, since the horseshoes were heavy, and had to be welded together and then sewn to a base, with feathers shooting out.”
© Christine Moore
© Christine MooreFor the 150th Kentucky Derby in 2024, Christine designed her most expensive hat – a $5,000 design with 150 hand-rolled silk roses that took 40 hours to create – and in 2025 had the opportunity to build “one of the most fun” when she showcased six award winning artisanal cheeses on a fascinator that resembled a charcuterie board, in partnership with Wisconsin Cheese Dairy Farmers of America.
“We built 21 pieces to showcase the six cheeses on each fascinator. Real cheese was not used but it had to look real and delicious. The design was a wonderful mix of realism and fantastical,” shared Christine.
The Kentucky Derby remains a key event in the southern social calendar, with Polly – who is based in Georgetown, Kentucky – sharing that it is one of the first events that gives attendees something to look forward to after a dark winter:
“In a culture that has become more casual by the moment, people relish the opportunity to dress up for a racing event and make memories with those they love.”
© GettyZanni Roberts Rassi, guest editor of the Kentucky Derby Style Guide, believes the Derby is an opportunity to embrace fashion as fun, and to take a risk while also understanding the assignment, calling it “southern elegance with a sense of celebration.”
“It’s one of the few events where dressing up is still part of the tradition—so there’s polish, personality, and a real sense of occasion. Think statement hats, beautiful dresses, sharp tailoring, bold color, florals, pastels, and details that feel joyful rather than overly serious. It’s festive and unapologetic.”
But she does have one note of caution: aim for “polished personality —not looking like you’re auditioning for a mint julep commercial.”
One strong statement piece is enough, with Zanni suggesting men stick to lightweight suits in linen, cotton, or seersucker in neutral colors and adding character through pieces such as a pocket square, patterned tie, loafer, or statement sock. Women should stick to a floral dress with a sharp silhouette, a beautifully cut skirt suit, or a statement hat styled with clean accessories and modern shoes work best.
The 152nd Kentucky Derby will take place on Saturday, May 2, 2026 at Churchill Downs in Louisville, Kentucky. Post time for the main race is expected to be around 6:57 pm local time.
Read the full article here
