Costly, hand-me-downs & sentimental: KY Derby hats come in all shapes & sizes
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2025 Kentucky Derby coverage
Click below to view more coverage from the Lexington Herald-Leader and Kentucky.com at the 151st Kentucky Derby on May 3 at Churchill Downs in Louisville.
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Kesha Johnson first attended the Kentucky Derby in 1989 as a Male High School student in Louisville.
Back then, it was less about the experience and more a means to an end — for three years starting when she was 15, she worked as an usher and a ticket taker to earn money to pay her marching band fees.
Thirty-six years later, she attended the 151st Derby as a spectator, wearing a hat tailor-made for her by a milliner in Nigeria.
“I searched many milliners. I wanted something very unique,” she said Saturday afternoon inside Churchill Downs.
Johnson, who now lives in Maryland, said she has a different hat for Preakness, this one designed locally.
Attending Derby as an adult is a “totally different experience,” she said. “We don’t appreciate the things we have in our own backyard. I appreciate the experience that the Kentucky Derby officers more now than I did when I was younger.”
For many, the Derby is as much about the horse-racing as it is a lavish fashion spectacle. Though this year’s was rainy, it was no less fashion-forward. Underneath ponchos and plastic hat coverings, bright colors popped and head pieces remained coiffed, for the most part.
Every outfit has a story, I learned Saturday, which happened to be my first time at the Derby. Those stories might not be as personal as Kesha’s, but they’re no less interesting.
The story behind Colleen Mulroe’s fascinator was both personal and interesting.
“My uncle’s late wife had this designed,” Colleen told me as the feathers, fuzzy tendrils and pom-poms bobbed on her head. “Since she passed away, we all wear her hats as a celebration of her.”
Mike Shannon said he and his late wife Helen went to their first Derby together in 1981 on a date.
“After two years there she said, I’m never going there again,” Mike said, laughing in front of the Twin Spires Saturday morning.
After they married, they became active members of the Kentucky Derby Museum and the Turf Club. Helen had close to 20 hats and fascinators custom made over the years for each of the Derby’s she attended.
Nearby, just inside the entrance, Stacy King’s outfit was turning heads. She struggled to walk without being stopped by strangers asking to pose with her for pictures.
It took her six weeks piece together by hand her hoop dress — a detailed patchwork of horses photos, lace and roses — and her hat, which included a miniature horse figurine and feathers. Quite the entrance for her first time at the Derby.
It was also Andrea V. Givens and Scott Leron Givens’ first time at Derby. And they arrived in style with coordinated outfits they paid more than $2,000 to have tailor-made.
The Baltimore couple said visiting Kentucky to go to the Derby has long been a “bucket list item.”
“I’m so excited to see all the fashion,” Andrea said.
“And pageantry,” Scott added.
“And to bet one the horses!,” Andrea said almost as an afterthought.
Wearing a lime-green dress and fascintator that looked like it might glow in the dark, Ashley Barton won last-minute tickets to this year’s Derby through her job.
Barton, who owns houses in Lexington and Bardstown, summoned help to find the perfect outfit from high school friends who now own a clothing boutique in Bardstown.
“In about 30 minutes, they had me dressed and in a hat,” Barton said. “I knew my friends would hook me up.”
Like many, Barton paid more for her hat than her dress — $240.
“It’s a statement piece, and you don’t have to fix your hair,” she said.
Tiffany Redmon’s $650 hat, which draped down her back, doubled as a guard against the rain.
Her last Derby was 2016. Like many Kentuckians, she more often attends races in the week leading up to Derby. This year, she went to Thurby, or Thursday Derby, too, wearing the same hat to both.
“It’s too fabulous not to wear again,” Redmon said.
This story was originally published May 3, 2025 at 3:28 PM.
