Source: Grace Bradley / Getty

The Kentucky Derby’s iconic hat tradition is a story woven from European influences and local flair. The roots reach back to the racetracks of England and France, where elaborate hats and refined fashion were as much a part of the spectacle as the horses themselves. When Colonel Meriwether Lewis Clark Jr. and his wife Mary founded the Kentucky Derby in 1875, they brought that sense of style home to Louisville. Mary Clark, a fashion influencer ahead of her time, famously rode through town in an elegant carriage, encouraging locals to don their finest attire—including hats—for the new racing event.

From that first Derby onward, hats became a mark of celebration. What started as a borrowed custom soon evolved into an unspoken tradition. Today, sporting a hat at the Derby isn’t just about style; many consider it a token of good fortune. The larger and more extravagant the hat, the bigger the luck, or so the saying goes. The Kentucky Derby Museum now showcases a kaleidoscope of historic hats that have graced the stands, each piece telling its own sartorial story.

STAY INFORMED! CLICK HERE TO SIGN UP FOR OUR NEWSLETTER!

Fascinators, those playful and often feathered headpieces, have also found their place at the Oaks, the spirited companion event to Derby day—but whether you opt for a subtle fascinator or an exuberant brimmed statement, your headwear is sure to turn heads.

This year’s gallery captures the creativity and color worn by stars like Simone Biles, Jonathan Owens, Star Jones, Joey Fatone, Tyrese Maxey, and more. Their looks blend high fashion with Derby tradition, making each ensemble fitting for The Kentucky Derby and Sunday service at church.

From the very first parade of hats to the dazzling displays of 2025, Derby headwear offers a chance for personal expression, celebration, and maybe even a little luck on race day.

RELATED STORIES:

Top 5 Moments In Kentucky Derby History

Simone Biles Gave Back-to-Back Fashion Moments & Big Wifey Vibes At The Kentucky Derby

The article ‘15 Hats and Looks From The Kentucky Derby That Could Be Worn to Church‘ was created with the help of Jasper.AI