The Kentucky Derby is 'like the Oscars, but for horses': Here's what it was like at Churchill Downs on race day

Fashion reigned supreme with colorful hats and bow ties filling the track.

Hundreds of flamboyantly dressed fans in stadium seating.
Fans in the stands at the 150th Kentucky Derby. (Jeff Schear/Getty Images for Churchill Downs)

The sweet smell of mint juleps! The colorful hats and bow ties! There’s nothing like the Kentucky Derby.

Held annually on the first Saturday in May, the 1.25-mile race at Churchill Downs, in Louisville, Ky., is often cited as “the most exciting two minutes in sports” and marks the first leg of horse racing’s Triple Crown series — which includes the Preakness Stakes, on May 18, and the Belmont Stakes, on June 8.

Known as the “Run for the Roses,” the Derby has been an American tradition since 1875. As a first-time attendee, I can say that the best tradition is the fashion-forward spectators whose ensembles have come to define the crowds in attendance at the racing event.

“It’s like the Oscars, but for horses,” Lena Williamson, from Louisville, Ky., told Yahoo Entertainment of the Derby. “I’ve been coming for years with my husband, rain or shine. There’s something so magical about it.”

Before the race, Wynonna Judd belted out the national anthem. It was a full-circle moment for the singer and Kentucky native.

Wynonna Judd and Cactus Moser appear to sing, on a white balcony among three large bouquets of red roses.
Wynonna Judd and husband Cactus Moser perform the national anthem before the start of the 150th running of the Kentucky Derby at Churchill Downs. (Rob Carr/Getty Images)

“This is number one on my list,” Judd told Yahoo before taking the stage. “I’m going to stand out there, look at everybody and go, ‘Oh my god, I can’t believe I made it.’ I’m from Kentucky. I grew up coming here. I was raised on welfare, I had nothing and now I have everything. This is America.”

Martha Stewart followed the performance by giving the traditional “Riders up!” command.

“I’ve been practicing,” Stewart, who was dressed from head to toe in Peter Cohen, said on the Kentucky Derby red carpet.

As expected, one of the highlights was sizing up the fashionable crowd, who did not disappoint.

“It’s beyond all expectations,” fashion critic Zanna Roberts Rassi, who authored the Kentucky Derby’s first-ever style guide for its 150th anniversary, told Yahoo. “It’s everything I dreamed of. Lots of pastels, preppy and floral — larger than life 3D florals!”

The hats are, of course, a huge staple at the Derby. From the 1800s through the mid 20th century, headwear was both a fashion statement and a day-to-day necessity.

Hat maker Christine A. Moore told me the famous look of today’s Derby hats — large and in-your-face styles — were originally patterned after the fashion of its English and French predecessors. Though their popularity saw a gradual decline in the '60s, they were incorporated back into Derby fashion in the '90s, becoming the over-the-top American look seen today.

A woman in large sunglasses holds a drink while wearing a hat that looks like an enormous red flower.
When it comes to hats, it's go big or go home. (Daniel Boczarski/Getty Images for Churchill Downs)
Three men smile for the camera and hold cigars while wear matching hats, bow ties and striped jackets.
For some attendees, the Derby was all about having fun with campy suits and a lot of personality. (Daniel Boczarski/Getty Images for Churchill Downs)

Tina Knowles, a frequent Derby attendee, said it’s a chance for men to express themselves sartorially too.

“The guys go all out!” she said, pointing to the colorful bow ties, fedoras and suits that have become a staple. “You never see guys dressed like this. It’s incredible.”

It’s not just about fashion, says Richie Sambora, former lead guitarist for Bon Jovi, who’s been coming to horse races since he was 12. For him, the Kentucky Derby has a way of uniting people. “Boy, do we need to be brought together in this world,” he said.

Several dozen people wearing flamboyant outfits with hats pose together in a room.
The reporter (far right) and a fashionable flock of Kentucky Derby attendees. (JP Davis/Derby Diversity Week)

“Everyone loves the Kentucky Derby, even if you’ve never been,” said music legend Smokey Robinson, who’s been coming to the event for 10 years. Despite his decade-long attendance, he doesn’t have a strategy for betting on horses. “If I like the number or the name, I just do that!”

NSync’s Joey Fatone, dressed in an all-white ensemble topped off with a white fedora, said the Derby inspires him to take more fashion risks. “I don’t normally wear white or cream, so this is not going to go well,” he joked.

Roughly 156,000 people watched on at Churchill Downs as Mystik Dan won in a three-way photo finish — only the 10th winner in the Derby’s history to win by that close of a margin. It was the largest crowd since 2018 and, according to ESPN, brought a whopping $210.7 million in bets laid down.