The Best (And Biggest) Hats At The 2026 Kentucky Derby |
Most horse racing fans head to Louisville’s Churchill Downs on the first Saturday in May watch the annual Run for the Roses. But plenty of show ponies are also there for the poses—showing off their Derby Day finery. And while those bold seersucker suits and vibrant floral sundresses may brighten up Millionaires Row and look great on TV, nothing tops a great topper at the Kentucky Derby.
And no style is out of fashion. There are wide-brimmed “Southern belle” hats, fascinators, fedoras, porkpies, bowlers, boaters and, of course, some homemade headwear that might be better left at home.
The tradition of dressing up for the first leg of the Triple Crown dates back to the earliest days of the Derby. In 1875, when Colonel Meriwether Lewis Clark Jr.—grandson of the famed American explorer—helped found the race, he took his inspiration from England’s Epsom Derby, which had formal dress codes for spectators, including hats. Clark believed that if those in attendance wore “full morning dress” it........