According to the Kentucky Derby's website, the hat-wearing tradition was started by founder Col. Meriwether Lewis Clark, Jr., who modeled the race after high-class European racing events.

The Kentucky Derby’s pageantry—from the broad hats to the tailored suits—is central to the race by design. Clark and his wife Mary, a socialite, promoted the Derby as a well-to-do affair.

From traditional hats to fascinators and headdresses, the best looks at the 151st running of America’s most fashionable sporting event. David Kasnic for The New York Times David Kasnic for The ...

Head-turning hats, bold, bright dresses, chic shoes and accessories were the basic elements of the well-dressed during the Kentucky Derby 2025.

Mrs. Woodrow Wilson, widow of the late President Wilson shown as she attended the running of the Kentucky Derby wearing a simple straw cloche hat at Louisville, Kentucky, May 6, 1933.

6:00. SIMONE BILES STUNNED WHILE IN TOWN FOR HER FIRST KENTUCKY DERBY. THE HATS AT THE OLYMPIC GOLD MEDALIST WORE ARE STILL THE TALK OF THE TOWN, AND NOW THEY CAN BE YOURS. WLKY’S ALEXIS MATHEWS ...

2024 Kentucky Derby weekend, horses may be in focus, but it's also all about the outfits. We are talking 150 years of fashion, after all. From the initial running of the Kentucky Derby in 1875 to ...

Kosair for Kids kicked off its fourth annual "Hats On for Healing" campaign Monday, transforming donated Derby hats into funding for the nonprofit’s Child Abuse Prevention Fund.

The hats that Biles wore during the weekend were made in Louisville by The Hat Girls. Now, Biles’ hats will go up for auction to benefit Kosair for Kids, a nonprofit with a mission to enhance ...