Kentucky Derby 2026 fashion trends: Designers weigh in on hats, Zendaya and JFK Jr.

The Athletic has stay protection of the 2026 Kentucky Derby.

Like a lot of the finest sporting occasions, the Kentucky Derby is as a lot in regards to the followers and spectators as it’s in regards to the sport. It’s a cultural second that blends thrilling motion, time-honored traditions and vivid aesthetics.

Fashion on the Kentucky Derby is not simply an integral a part of the expertise; it is also a full-emotional-contact sport.

“The Derby is a different kind of spectator sport,” says Zanna Roberts Rassi, a fashion journalist and visitor model editor for the 2026 Kentucky Derby Style Guidewho can be jet-setting from the Derby on Saturday to the Met Gala simply two days later.

“It’s an explosion and a celebration of self-expression, an optical feast. Your Derby outfit is a quick cut to your character and your personality.”

We spoke with Rassi and others, together with couture milliners and fashion influencers, to get their learn on the highest seems to be and fashion tendencies on the 2026 “Run for the Roses.”

And this does not simply need to be for these at Churchill Downs on Saturday. For these at house, have a watch social gathering and gown up! Gigi Burris, a designer and proprietor of Gigi Burris Millinery, suggests having a “best-dressed contest” at your Derby watch social gathering.

“Don’t bring a less-than to a watch party,” Burris says. “Bring your Churchill Downs best.”

Here are their strategies.

“Main character energy”

Every knowledgeable we spoke to stated this 12 months’s look is all about “main character energy” — this intentional kind of maximalism is exhibiting up on runways, trickling right down to crimson carpets and occasions just like the Derby.

And if ever there was a spot to be unabashed and unapologetic in model, it is at Churchill Downs on that first Saturday in May.

“We are pretty consistently seeing an appetite for BIG,” stated Burris. “People want something that is going to turn heads, make them the center of attention.” Burris has designed hats for the likes of Alix Earle and Britainy Beshearthe spouse of Kentucky Governor Andy Beshear.

One nice technique to search inspiration? “If you have a favorite celebrity, channel them in a main character way,” Rassi says.

Here are methods to attain this pop in your look:

huge brims

For hats on the 2026 Derby, Burris says, “Big brims are the standard.”

“Ask yourself, ‘How does Zendaya wear a hat?’” Rassi says. “It’s burned in my brain the Met Gala outfit Zendaya wore last year. It was a simple three-piece Louis Vuitton suit with a wide-brimmed hat, with 70’s swagger.”

How to make it yours: Rassi suggests on the lookout for five-inch-plus brims with full protection and trying out Louis Vuitton for inspiration.

Feathers

A giant technique to hit that important character vitality is by strategic use of… feathers!

“Feathers 100 percent,” says Rassi. “When we say main character energy, we’re seeing a big tactile texture moment. Think Demi Moore at the Oscars, think Teyana Taylor in the Chanel with the black and white feathers, or Nicole Kidman and the pink feathers.”

Teyana Taylor went huge on feathers in a Chanel robe on the 2026 Oscars. (Mike Coppola/Getty Images)

How to make it yours: “What would Teyana Taylor wear to the Kentucky Derby?” Rassi continued. “Now, I’m not saying go in a full Chanel couture gown; I’m just saying take an element from her look, like feathers. That simple element could belong on the hat, it could belong on the base of the dress, it could be on the sleeves.”

Creative coloration blocking and quirky coloration selections

Runways and crimson carpets are stuffed with sudden colours this 12 months, with the important thing to the development being intense saturation. For instance, keep away from mixing a pastel up prime and a main on the underside. Go with 110 p.c saturation on each to show up the quantity.

Jessie Buckley wore a customized Chanel robe designed by Matthieu Blazy to the 2026 Oscars (Patrick T. Fallon / AFP by way of Getty Images)

“Jessie Buckley at the Oscars was one of my favorites,” Rassi stated. “She did the unique color combination in a very elegant way. Orangey red and pink is FUN.”

Unique colours might embrace purple, lime, chartreuse, orange, scarlet and violet.

“Tessa Thompson at the Golden Globes wore a Balenciaga gown in a chartreuse type color that her stylist said they weren’t even sure what to call it,” Rassi stated. “It was almost scale-like, and each was meticulously trimmed.”

Tessa Thompson wore a chartreuse (ish?) Balenciaga robe designed by Pierpaolo Piccioli on the 2026 Golden Globes. (Frederic J. Brown / AFP by way of Getty Images)

How to make it yours: Rassi says something from Alessandro Michelle’s assortment for Valentino is an effective reference. “For guys, color blocking works well, too,” says Rassi. “A baby blue jacket with a khaki trouser is kind of fun.”

“Polished personality”

Zendaya’s Met Gala look final 12 months additionally exemplifies a key facet of 2026 maximalism: Not all maximalism is equal. “More is more” shouldn’t be essentially the vibe, however reasonably, as Burris says, “something more considered, sophisticated.”

“Try a pop of color on the hat and keep the rest of the look almost neutral,” Rassi stated. “Just pick one element. You don’t need to do the feathers and sparkles and florals. Pick a lane and double down on that instead of trying to do too many elements.

“Pick a lane and go full gallop.”

Clients are looking for looks that are customized, put-together and personalized. Instead of over-the-top embellishments, they are looking for something with “no less impact, but more intentional and elevated,” Burris said.

This year, that impact is less about complex embellishments and more about materials. Burris describes shiny straw hat she designed this year with lurex (a metallic, shiny fabric) woven into it. She is emphasizing bold shapes but with refined, simple trim, like foxglove with couture featherwork, or a big brim with restrained metallic ribbon.

“When you arrive at the track, you want to look considered,” Burris says. “That’s what is going on to make you actually flip heads; the small print actually matter.”

The same goes for menswear.

“For those wearing masculine styles, you don’t want to look like you’re auditioning for a mint julep commercial,” said Rassi. “One sturdy assertion is sufficient. That might be a pointy swimsuit in a lighter cloth however a popping coloration.”

And speaking of the guys….

Brooches for menswear

For men? Try a brooch!

“On the carpet at the Oscars, it seemed like every single guy had a brooch, and if you didn’t, you were underdressed,” Rassi said. “Guys, check out Pedro Pascal’s Oscars’ Chanel ensemble with a feather brooch. Take a very good take a look at that, and go to work.”

Pedro Pascal in a customized Chanel ensemble on the 2026 Oscars with a feather floral brooch. (Julian Hamilton/Getty Images)

Florals for spring… however *at present* ground-breaking

Florals are to the Kentucky Derby what sneakers are to basketball: the important aesthetic.

Several of the folks we spoke to joked in regards to the basic line from “The Devil Wears Prada”: “Florals? For spring? Groundbreaking.”

But, says Rassi, there are methods to make a floral look actually distinctive.

“So if you’re going to do florals,” Rassi says, “take a look at Anne Hathaway at the Oscars. She did it in an interesting way with a black base and a light floral. That is a unique way of taking on florals.”

Anne Hathaway and Anna Wintour on the 2026 Oscars. Hathaway wore a Valentino black floral robe created by Alessandro Michele (Patrick T. Fallon / AFP by way of Getty Images)

“Florals are always in,” Burris says. “We work very closely with a fourth-generation flower workshop in the heart of New York City’s garment center, M&S Schmalberg, which is a reminder that dressing up for the Derby is a great way to support local craft.

“We work with local ateliers and craft workshops, whether that’s having custom-dyed feathers or beautiful silk flowers commissioned in a special fabric and type of flower. It’s a great way to support local artisans and small businesses.”

Kennedy-core American prep: Skirt suits, pillbox hats, JFK Jr.

This look spans decades but is tied together by one American family: the Kennedys. Think Jackie Kennedy Onassis for the more traditional look, and Carolyn Bessette Kennedy and John F. Kennedy Jr. for the more modern, streamlined 90s vibe.

“The reference point for an audience would be a ‘Love Story’ revival,” Rassi says, referencing the 2026 hit Netflix sequence about JFK Jr. and Carolyn Bessette. “It’s that polished prep, the American classics. A little country club, a little old money, a little Miss Came-with-a-horse-and-an-estate.”

Paul Kelly and Sarah Pidgeon as JFK Jr. and Carolyn Bessette on the set of Ryan Murphy’s “American Love Story” (Photo by Jose Perez / Bauer-Griffin / GC Images)

Skirt fits

Rassi suggests a skirt swimsuit and a fantastic silk scarf for the Jackie O. vibe.

“We are seeing a lot of skirt suits,” Rassi says. “They were definitely prominent on the runway, from Chanel to Christian Dior. They are the silhouette of the moment.”

How to make it yours: Rassi suggests a cropped jacket with a fantastic, sharp pencil skirt — “it could be tweed, it could be floral” — or a dropped-waist skirt for one thing distinctive. “At Chanel’s most recent buzzed-about show, we saw the skirt suit completely reimagined,” Rassi says.

For a extra 90s, uncooked CBK look: “Choose a slip dress, wrap a crew neck around your shoulders and wear a loafer. Very Calvin Klein minimal.”

Vintage hats

For males, obtain this basic American look with a newsboy flat cap à la JFK Jr.

For ladies, pillbox hats are again!

“What I’ll personally be wearing is a pillbox,” Rassi stated. “It’s the biggest trend not only for the Kentucky Derby, but it was huge on the runways. Jennifer Lawrence was seen “taking her baby on a walk in a pillbox.”

America 250 theme?

Woodford Reserve has a specifically designed Kentucky Derby-edition bottle with a red-white-and-blue motif celebrating “American 250.”

“It will be interesting to see if the fashions at Churchill have more reds and blues and ivories woven in,” Burris stated. She stated they’re seeing a number of navy in shopper requests this 12 months.