How a Kentucky Derby hat designer began her career after experiencing her first derby event

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LOUISVILLE, Ky. () — A hat or a fascinator — whatever name you choose to call it — is a crucial part of any outfit for the Kentucky Derby. Diana Heron, born and raised in Kentucky, got into the hat-making business after she was invited to her first derby.

Heron says, “In 2011, my son’s grandmother invited me to the Kentucky Derby and I was freaking out, like, what am I going to wear?” She went to a local fabric store and gathered everything that looked good together to her and she crafted her own fascinator.

The definition of a fascinator is “a woman’s light, decorative headpiece consisting of feathers, flowers, beads, etc. attached to a comb or hair clip.” And Heron’s first creation turned out so well people at Churchill Downs stopped her to ask where she got it. When they found out she made hers, they wanted one for themselves too. “They asked me ‘Do I have a business card? How long have you been doing this?”

And so, Derby Diana’s was born. Since then, she’s made hundreds of hats, including one ‘The Real Housewives of Atlanta’ star Sanya Richards-Ross wore at the Derby. “I really feel like that’s where my business picked up. A lot of blogs, the Bravo blog is huge, they mentioned me. I was in Essence magazine. Ebony magazine.”

Heron says she gets inspiration from her father’s native Jamaica. “Just that rich color really inspired me just as art, colors, and all the things.” She says she’s always considered herself a Derby Baby. Her birthday is May 2. And her side hustle keeps her very busy, but her hats are not for someone who doesn’t want to stand out.

You can see hats like Diana’s at the 2025 Kentucky Derby — which is the 151st Run for the Roses — Saturday, May 3 on . It will also stream on Peacock.