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.

While some crafted their headgear from yard sale finds or eBay searches, others looked to custom pieces by the likes of veteran milliner Christine A. Moore. “Theatrical fashion is what I’m really known for…and I think my detail is what I’m really known for,” Moore told Vogue. Moore’s style is highly feminine and dramatic; thanks to her background in costume design on Broadway and assisting legendary theatrical milliner Rodney Gordon. Moore sells her handmade designs from her iconic local boutique Rodes, to both Derby attendees and Royal Ascot-goers across the pond in Britain. For the annual event, her millinery goes through about 700 yards of silk. Some of her most opulent creations can take around 40 hours to make, with prices topping $5,000—the average price hovers around $1,100—but her signature designs are passed through generations of Derby queens.

“When I saw [my] dress from AFRM, I knew it needed its moment for Derby weekend,” says Connor Perry, the current reigning Miss Kentucky. “The vibrant pinks and reds, the rose pattern—it was too good to be true!” Her custom hats were made by Melissa Huff with Mad Hatter 502 and Mamili Boutique in Louisville, Kentucky for both races. “I showed her the dress and shared a bit of inspiration from her past work—she ran with it!” Perry says. “The way she weaves together textures and color palettes is truly brilliant. She’s an artist, and I don’t think a more perfect fascinator exists for the occasion.”

What did guests of the day pair with their jaunty chapeau and rose-studded bonnets? The peplum dress made a huge comeback while boho cork wedges (wet grass-appropriate) were also seen traversing the fields. Frocks were fuchsia and brave whites, while polka dots were an emerging trend.

The heavy rain didn’t dampen spirits or sartorial splendidness. Below, see the best Kentucky Derby 2025 looks.