The Most Over-the-Top Hats at the Kentucky Derby Through the Years

Every year guests don their best — and oftentimes, craziest — hats for the Kentucky Derby in Louisville.

Hats have been synonymous with the annual horse race since it was established by Col. Meriwether Clark Jr. 1875. Inspired by British races, Clark Jr. and his wife helped kick off the now annual tradition of wearing hats for the occasion. Over the 150 years since then, hats have become bigger and bolder as guests leaned into the spirit of competition through the staple accessory. Satellite viewing events for the Derby in other cities are also anchored by festive headpieces, with accompanying competitions that can rival the actual race itself.

Here’s a look at some of the most outlandish millinery that guests have worn to the Derby throughout the years, from models of Churchill Downs racetrack’s twin spires to scenes of the racetrack and other Bacchanalian displays. And with over 150,000 guests expected to attend the race, there will be plenty more to come.