Kentucky Derby: The Most Fabulous and Hattiest Hats of the Day at the Races

While it’s inevitable that hats will fall in and out of fashion, and trend cycles will dictate their size and stature, it’s safe to say the Kentucky Derby 2025 is where we saw the hat in full sartorial excellence.

The annual Churchill Downs horse race is now in its 151st year, with almost 150,000 attendees heading out to watch their favorite jockeys, the thoroughbreds, and underdog colts attempt to win at one of the most prestigious horse races in the world. But with that, it’s also a pageant for some of the world’s best hats and fascinators.

The Kentucky Derby 2025 style guide asks that guests celebrate “a modern blend of timeless elegance and expressive flair with pastel tones, jewel accents, and bold silhouettes.” But the star of the show? The Derby Day hat. The Derby’s guest style editor, Zanna Roberts Rassi, put together a handy guide for people whose sport is more fashion that the horses of the day. Hats, first: She recommended cartwheel hats—an exaggerated disc silhouette, with a small crown and wide brim that sits on the head at an angle. “Sculptural, little mystery, lots of drama.” The small pillbox style hat—which we’ve seen from Prada to Altuzarra—was also approved for race day, as well as more brimless shapes and ladylike, paired down embellishments. Veils, headscarves, and turban style hats were also on Zanna’s style list. In terms of texture: Think weaves, raffia, and straw. Colors? It’s anyone’s game, whether a more refined palette of ivory and toffee, or seasonal pastels, pistachio greens, on-trend butter yellow, and powder pink.

Despite the downpours and terrible weather, both veterans and first-timers persevered: the grandstands and damp grass were a sea of colorful, ornate headpieces and surreal shapes, underneath which they placed their bets and cheersed mint juleps. Some wore their fascinators atop their rain ponchos, or used their fantastically wide brims as umbrellas themselves. Silk rosettes and feathered tips, natural textures, and miniature animal sculptures (swans, horses, even a rhino) featured on the crowns. Roses are a year-on-year trend: the Kentucky Derby is sometimes referred to as the “Run for the Roses”—a reflection of the 544 roses the winner is presented with.