Technically, the Kentucky Derby is about horse racing. While wearing a hat was once a functional choice for attendees (it ...

A woman wearing a red, black and white Kentucky Derby hat walks to her seat at Churchill Downs on Saturday. (Bryan Woolston / Associated Press) Big flowers tend to dominate hats at the Kentucky Derby.

Jenna Moore wore a large black and pink Derby hat on Kentucky Derby Day at Churchill Downs in Louisville, Ky. on May 6, 2023.

First came the wide-brimmed hat, then the fascinator, followed by the hatinator. Now the Fromaginator is taking a run at 2025 Kentucky Derby fashion.

I sported a vest, tie and a charming little straw hat, while Trish stunned in a black-and-white dress paired with a striking “fascinator” hat.

Anyone tuning into the Kentucky Derby each May sees not only plenty of horses, but plenty of hats. The fashion at Churchill Downs is, at times, just as impressive as the fastest horses in America ...

The Louisville Youth Group is using the Derby season to raise money for transgender children.

There won’t be any Black jockeys in the Kentucky Derby. That’s not new. Black jockeys dominated 19th-century American horse racing, but racism chased them away, and undoing that damage has ...

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.

Heading to the Kentucky Derby or a themed party? These stylish Amazon picks — from dresses to fascinators — have you race-day ready.