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Head-turning hats, bold Kentucky Derby dresses lead fashion at 150th Run for the Roses



Fashion has been nearly as important as the horse race at Churchill Downs since the first Kentucky Derby in 1875. Now 150 years later, some might argue the two are equal. 

“Fashion at this year’s Derby is so elevated that it’s going to solidify the Kentucky Derby in American culture,” said Christine A. Moore, a Featured Milliner of the Kentucky Derby. “And fashion is only going to get better from this point on, I guarantee it.”

Head-turning hats, bold bright dresses, chic shoes and accessories were the basic elements of the well-dressed Kentucky Derby weekend race fan who showed up and showed out spectacularly at Churchill Downs on Thursday, Friday and Saturday.  

While a killer dress in bold colors and patterns galore is a must, what sets the Kentucky Derby apart from other elegant events is how you top it all off.

Bill and Angie Burns, from Jeffersonville, Indiana, have been coming to the Derby for 20 years. Angie says the hat “is the most important” and always chooses that first when selecting an outfit.

“I usually do a fascinator. I’ve done big hats in the past, but lately it’s all been fascinators,” Angie Burns said.

The couple, coordinating in shades of pink, said they take turns taking the lead on their Derby Week outfits.

“It depends on who shops first,” Bill Burns said with a laugh.

For the 150th Kentucky Derby, wide-brimmed hats were again the most popular style, but smaller fascinators worn on a headband gave the traditional Derby hat a run for its money.

Olivia Doss and Tim Doss, of Floyds Knob, Indiana, looked picture-perfect in a carefully coordinated ensemble that featured pale pinks, light blues and a pop of mint green. While some spent months choosing their outfit, the Doss couple did it on the fly. They bought tickets to Thurby on Wednesday night and pulled together their carefully coordinated outfit in hours.

“I just completely go with what she says, Tim Doss said. “She used to own a boutique so I defer to her.”

You may like: Here’s how to order The Courier Journal’s ‘150 Years of the Kentucky Derby’ book

Men may not have as many creative options as women in the hat department, but a fine-looking fedora with colorful accents will make them feel part of the celebration.

Bill Burns said this is only the second or third year he’s worn a hat. “I am not a big hat person, but it’s a time I can wear a hat and not feel like I am sticking out. I blend in.”

Because of the historic significance of the 150th Kentucky Derby, shades of red — a nod to the nickname “Run for the Roses” — and silk rose embellishments were on full display throughout the race track.

Alexandra Cantelmo and Michael Cieri spent a great deal of time on their outfits for their first Kentucky Derby.

“I ordered close to 50 dresses off Amazon until I came up with this floral dress with red roses,” Cantelmo said. “I scoured the internet for months to figure out how you all dress in Kentucky for the Derby.”

Fans started early, months ahead of the races, to ensure every piece of their Kentucky Derby wardrobe was a stunner.

“Last year was my first year for the Derby and I would say my takeaways are be versatile, have pockets to hold plenty of stuff, and make sure you look good,” said David Maldonado of Chicago.

From head to toe, there is nothing quite like dressing for “The Most Exciting Two Minutes in Sports,” and nothing like cheering on your favorite in style.

“Derby week is the best week in the entire calendar year,” said Dana Newman of Louisville. “Be comfortable, step outside of your comfort zone, and add a little razzle-dazzle, make sure you feel spectacular and you are sure to have fun!”

Reach features reporter Kirby Adams at

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