Kentucky Derby 2025 fashion trends from Timothée Chalamet to 'Wicked.' Designers weigh in

Churchill Downs has trademarked the Kentucky Derby as “the most exciting two minutes in sports.” But, in the words of Louisville-born milliner Mary Julia Kaiser, “It’s not just a two-minute moment for Louisville. It’s a citywide season.”

School is canceled the Friday before race day, restaurants are slammed, hotel prices skyrocket and a thriving hat-making industry is churning out beautiful, painstaking work. For those in attendance, the Kentucky Derby is much more than just a race.

“People plan their outfits for the Derby much like a wedding,” says Jenny Pfanenstiel of Formé Millinery. “It is not just another day at an ordinary event; it’s the Kentucky Derby!”

“The Derby is a different kind of spectator sport,” says Today Show style correspondent Zanna Roberts Rassi, who is the returning guest editor of the Kentucky Derby Style Guide. “It’s an explosion and a celebration of self-expression, an optical feast.”

That optical feast is prepared by many local and international artisans who come together to create each year’s Derby fashion. We reached out to them to learn about the culture surrounding this unique sport — and, of course, to get the inside scoop on this year’s biggest fashion trends.

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‘It’s more than just fashion. It’s about people.’

The Kentucky Derby sustains a small but thriving community of craftspeople.

“There are micro-economies that live on this event,” says Gigi Burris, who runs her millinery atelier in New York City. Last year, she made the hat worn by social media A-lister Alix Earle. Burris could be described as a blueblood of the millinery world, educated at Parsons School of Design in both New York and Paris, working with top brands and fashion designers and providing headwear for celebrities like Rihanna, Lady Gaga and Madonna.

But in a call with her, Burris intentionally shifts focus from the craft to the craftspeople. “Millinery is a dying trade, and there are fewer and fewer resources for us as an industry to develop talent,” Burris says. The ancient tradition of master craftsmen passing on their knowledge to younger apprentices is drying up, she says. “We could lose those intergenerational skills.”

Jessica Schickli, owner of Louisville-based Hat Haven, is one designer who benefits from such a tradition. Her hat-making is a skill passed down from her mother like a living heirloom. She has witnessed the Kentucky Derby evolve from a local event into the international spectacle it is today. Schickli keeps bringing our conversation back to the local roots of the Derby, the history that she weaves into her hats.

“I have hats with jockey silk remnants in them,” she says. She tells me not to miss a trip to Wagner’s Pharmacy when I’m in town.

Tony Wilson-Browder is a local milliner from Tony Leon Designs whose roots in “hats and horses” go even further back in his lineage. His grandfather, Robert C. Caldwell II, was a horse trainer recognized in the “Chronicle of African Americans in the Horse Industry Oral History Project.” Wilson-Browder remembers growing up in Georgetown, Kentucky, going to work on the horse farms with his grandfather and falling in love with horses. He loved the hats his mother wore to their Pentecostal church.

“In my curiosity, being the Aquarius that I am, I would take her hats apart and put them back together a different way,” Wilson-Browder says. “She loved it, and I fell in love with millinery.”

Now he runs his hat-making business with his husband of eight years.

Patricia Standard has taken apprenticeship into her own hands and neighborhood. Educated at the Academy of Art University and known by her professors as “Miss Textile” thanks to her singular designs, Standard approaches millinery with a community leader’s eye for the potential around her. She opened her shop, Crown by Standard, on Raggard Road in Louisville and welcomes young people from the neighborhood who are interested in learning from her.

“Even though they may not want to be milliners or textile designers,” Standard says, “all of these things can open doors for them.”

Louisville-born Mary Julia Kaiser, a nurse practitioner and mother of six, recalls Derby week from her kindergarten days, when they would make papier-mâché horses and race them around the classroom. She says hat-making “kind of fell into my lap” one year when she went to a Derby event and was underwhelmed by the hat she had ordered on Amazon. So she “dressed it up.” It grew from there when her sister encouraged her to open an Etsy shop in 2017.

In 2024, TODAY’s Hoda Kotb and Jenna Bush Hager wore Kaiser’s bouquet-inspired hats. Now, she’s one of the Derby’s featured milliners with her company, Derbyologie.

“It’s been a joyride,” Kaiser says. “One pinch-me moment after the next.”

Diana Heron is another local who has seen her handiwork on celebrities. Owner of Derby Dianas, Heron’s business grew through word of mouth until she landed in the path of celebrity stylist Ryan Christopher, and designed a hat for Olympic and world champion track and field athlete Sanya Richards-Ross.

“These events [like the Derby] support the local economy in the sense that a really niche craft industry hangs on this,” Burris says. “It’s more than just fashion, it’s about the people.”

While, as Burris says, these craftspeople rely on the business of the “first Saturday in May,” the Kentucky Derby’s success, conversely, hangs on these local artisans. It’s a partnership woven together as naturally and sturdily as the woven wire and sinamay that form a Derby hat.

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We asked, they answered: The top trends at this year’s Derby

Last year’s trends were influenced by the release of Beyoncé’s “Cowboy Carter” album and the “Barbie” movie. So, we asked the experts: What can we expect this year?

1. Pastels, pastels, pastels

The first trend on every designer’s lips: “Pastels.”

“Pastels again? Groundbreaking,” Roberts Rassi says with a laugh, referencing the much-loved Meryl Streep quote from “The Devil Wears Prada.”

But pastels, Roberts Rassi quickly amends, are a classic because they are so versatile. She emphasizes looking for “cool pastels” like blush pinks, pistachio green and butter yellow. The color palettes popular after pandemic shutdowns were vivid, bright and almost saccharine. But the “Barbie”-influenced hot pinks are now fading away for softer shades.

“Pale pink is the hottest color,” says Pfanenstiel.

2. ‘Wicked’ whimsy

Move over, “Barbie”! The pastel trend is, perhaps, largely thanks to another blockbuster movie: “Wicked.” Ariana Grande’s wardrobe in the smash movie musical includes a range of soft pastels, but most iconically, blush pink.

“I think we should definitely be saying thank you to our ‘Wicked’ sisters,” Roberts Rassi says. “The fairy tale aesthetic and the method dressing from Cynthia [Erivo] and Ariana [Grande] on the red carpet have had a major impact.”

Look for blush pink, bubble hems, whimsical florals, veils and every shade of green on the spectrum, from pistachio to neon. In the spirit of Erivo’s aesthetic, I’ll have an eye out for unique nail art on the ground at Churchill Downs.

3. Old Hollywood

Look no further than January’s Golden Globes red carpet: Old Hollywood glamour is back. Think: long opera gloves, vintage dresses from the ‘50s and ‘60s, ball gowns, dramatic draping and voluminous skirts and hairstyles featuring soft lines, waves and bouffant. Wilson-Browder describes his favorite trend as “classic, timeless, less is more.” One of his biggest influences is Jackie Onassis.

4. Pattern watch: Polka dots and florals

While florals are a constant at the Derby, Roberts Rassi describes this year’s floral trend as “wallpaper floral prints.”

“Imagine a Southern Living bouquet on your head,” says Kaiser. “People will ask, ‘How does that stay on your head?’”

And, speaking of old Hollywood style, polka dots are back!

5. ‘Dandyism’

The day after the Kentucky Derby, stars will walk the Met Gala red carpet. This year’s Met Gala theme is “Superfine: Tailoring Black Style,” drawing inspiration from Monica L. Miller’s 2009 book “Slaves to Fashion: Black Dandyism and the Styling of Black Diasporic Identity.” Colman Domingo — known for his elite, theatrical, dandified red carpet style — is a co-host along with Lewis Hamilton, A$AP Rocky, Pharrell Williams and Anna Wintour, with LeBron James serving as co-chair.

“Guys should bring the dandy of it all,” Roberts Rassi says. “Don’t be afraid, bring the theater, bring the persona, bring the pocket squares, bring the cane! If this isn’t an occasion to do that, then when is?”

6. Masculine monochrome

For those going with a masculine styling who aren’t ready for dandyism, monochromatic is the trend of the hour. Traditionally, men mix and match prints for the Derby, combining lots of colors like a blue suit, pink tie and yellow shirt. This year, thanks to celebrities like Timothée Chalamet and his head-to-toe butter-yellow Oscars look, men are going monochrome. Roberts Rassi says the key here is to go all in, with a full monochromatic look: the tie, the shirt, the shoes, all of it.

7. Neutrals. No, really!

When you think of the Kentucky Derby — and Southern style in general — neutrals do not often come to mind. But this year, designers say, neutrals are in high demand. Burris developed a collection with Woodford Reserve featuring all neutrals, allowing people to wear their hats with a variety of different looks. She says she focused on neutrals like taupes, creams, cocoa and soft beige.

“A neutral is something clients can re-wear,” Burris says.

8. Architectural shapes and illusion hats

“I call the style ‘Swirled sinamays and branching bouquets,’” says Kaiser. “Geometric and architectural pieces with swirled fabric manipulation have sold a lot this year.”

9. Boaters and fascinators

“The fascinator trend continues to sweep,” says Kaiser. “I’d say 90 percent of what I do are fascinators.”

A fascinator, she points out, doesn’t equal small. They can be quite large and “have a lot of impact and drama,” but without the hat head. Most of the designers I spoke with point to the British royal family — and Princess of Wales, otherwise known as Kate Middleton — as the driving influence behind the fascinator trend. But this year, another classic hat is rising: the boater.

“We’re returning to more classic styles,” Roberts Rassi says. “The boater style has been very popular this year, with Kate Middleton wearing more boaters and Melania Trump’s style for the inauguration.”

10. Traveling beyond the traditional

Heron says she loves to play with fresh designs and bold takes beyond the traditional Derby look.

“For me,” Heron says, “I learn a lot from the Nigerians. They have excellent milliners, and I love watching hours of YouTube videos showing me all the different things to do, like making leaves or taking a series of feathers and curling them into a flower.”

In the end, they all advise just going for it. While this year’s color palette is softer, the spirit of Derby fashion remains one of self-expression.

“People do get very brave at the derby,” says Roberts Rassi. “My best advice: You do you.”

Standard says, “For me, personally, I don’t follow a trend. I don’t even look back at my old designs because I do not repeat anything. I get all my supplies, put them all in front of me, and then let the designs come to me. Some people don’t follow; they go with what’s in their gut.”

“Truth is, you’ll never see someone in a bad mood who’s wearing a hat,” says Kaiser.

(Top photo: Illustration: Dan Goldfarb / The Athletic; Formé Millinery, Leandro Lazada, Jessica Ren Vaughan, Andrew Kung Group)