The uninitiated soon discover that a Kentucky Derby hat should never be an afterthought ... "This rain is not funny right now, but it's going to be funny tonight," said Jed Rainey.

While classic Kentucky Derby hats are usually decorated with anything from feathers to flowers, horse-themed headgear has been a popular choice over the years. Check these out!

wear funny hats. Yes, the Kentucky Derby is far more than just a horse race. It’s a cultural touchstone run each spring in Louisville, Kentucky, as the first leg of the vaunted Triple Crown.

The official Kentucky Derby website has a fairly lengthy explainer ... It's the use of "exuding humorous themes" instead of "funny hats" that lets you know how classy this event truly aspires ...

At the Kentucky Derby, where thoroughbred horses come second to fashionable hats and dresses, you can be both. Although fashion at the Kentucky Derby has evolved over the years, hats and ...

The 151st Kentucky Derby is almost a week away. Attendees will be showing up to Churchill Downs in their best attire, which includes the most notable piece, bold, beautiful and eye-catching hats.

Horse racing fans during Kentucky Derby 151 at Churchill Downs May 3, 2025. Kesha Johnson wore a blue, gold and silver hat from a Nigerian milliner during Kentucky Derby 151 at Churchill Downs May ...

Although horses may be the stars of the Kentucky Derby, hats take center stage at the 151-year old horse race in the American heartland. In Kentucky, hats—the wilder the better—are central to ...

Rain at Churchill Downs altered the plans for many at this year’s Kentucky Derby, with attendees like Candice Daugherty using ponchos to cover their dresses, while their hats still had a chance ...

Women wait to compete in the hat contest Saturday at Kentucky Derby on Worth. / Meghan McCarthy / USA TODAY NETWORK The 151st Kentucky Derby takes place this Saturday. As the first leg of the ...