Kentucky Derby 2026 fashion trends: Designer hats, focus on Zendaya and JFK Jr.

Like most great sporting events, the Kentucky Derby is as much about the fans and spectators as it is about the game. It’s a cultural moment that blends thrilling action, time-honored traditions and vivid aesthetics.

Fashion isn’t just an integral part of the experience at the Kentucky Derby; It’s also a full-emotional-contact sport.

“Derby is a different kind of spectator sport,” says Zaina Roberts Rassi, a fashion journalist and guest style editor. 2026 kentucky derby style guideWho will fly to the Met Gala on Saturday, just two days from the derby.

“It’s an explosion and celebration of self-expression, an optical feast. Your derby outfit is an instant expression of your character and your personality.”

We spoke to Rassie and others, including couture milliners and fashion influencers, to learn about the top looks and fashion trends in the 2026 “Run for the Roses.”

And it shouldn’t just be for those who were at Churchill Downs on Saturday. For those at home, throw a watch party and get dressed up! Gigi Burris, a designer and owner of Gigi Burris Millinery, suggests holding a “best dressed contest” at your derby watch party.

“Bring a bare minimum to a watch party,” says Burris. “Bring your Churchill Downs best.”

Here are his suggestions.

“Main Character Energy”

Every expert we spoke to said this year’s look is all about “main character energy” — this deliberate kind of maximalism is showing up on runways, red carpets, and events like the Derby.

And if there’s ever a place where brazenness and irreverence can be found in style, it’s at Churchill Downs on the first Saturday in May.

“We continue to see an appetite for bigger,” Burris said. “People want something that grabs everyone’s attention, makes them the center of attention.” Burris designs hats for people like these alix earl And brittany beshearWife of Kentucky Governor Andy Beshear.

A great way to get inspired? “If you have a favorite celebrity, feature them as the main character,” says Rassi.

Here are ways to get this pop in your look:

big banks

As for the hats in the 2026 Derby, Burris says, “large brims are the standard.”

“Ask yourself, ‘How does Zendaya wear a hat?'” says Rassi. “I’m reminded of the Met Gala dress Zendaya wore last year. It was a simple white suit, but she had a 20-inch brimmed hat.”

How to make it yours: Rassi suggests looking for brims over five inches with full coverage and checking out Louis Vuitton for inspiration.

Wing

A great way to influence the main character’s energy is through the strategic use of wings!

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

Teyana Taylor looked stunning in a Chanel gown at the 2026 Oscars. (Mike Coppola/Getty Images)

How to make it yours: “What will Teyana Taylor wear to the Kentucky Derby?”. Rassi continued. “Now, I’m not saying wear a full Chanel Couture gown; I’m just saying take one element from her look, like a feather. That simple element could be on the hat, it could be at the base of the dress, it could be on the sleeve.”

Creative color blocking and quirky color choices

Runways and red carpets are full of unexpected colors this year, the key to this trend is intense saturation. For example, avoid mixing pastels on top and primaries on the bottom. Place 110 percent saturation on both to increase the volume.

Jessie Buckley wore a custom Chanel gown designed by Matthew Blasey to the 2026 Oscars (Patrick T. Fallon/AFP via Getty Images)

“Jessie Buckley was one of my favorites at the Oscars,” Rassi said. “She did a unique color combination so beautifully. The orange red and pink is fun.”

Unique colors may include purple, lemon, chartreuse, orange, red and purple.

“Tessa Thompson at the Golden Globes wore a Balenciaga gown in a chartreuse-type color, which her stylist said she didn’t even know what to call it,” Rasi said. “It was almost like scale, and each one was carefully cut out.”

Tessa Thompson wore a chartreuse(ish?) Balenciaga gown designed by Pierpaolo Piccioli at the 2026 Golden Globes. (Frederick J. Brown/AFP via Getty Images)

How to make it yours: Rassi says anything from Alessandro Michele’s collection for Valentino is a good reference. “For guys, color blocking also works well,” says Rassi. “The baby blue jacket with the khaki trousers is kind of fun.”

“Outstanding Personality”

Zendaya’s Met Gala look last year also exemplifies a key aspect of 2026 maximalism: not all maximalism is the same. “More is more” is not necessarily a sentiment, but rather, as Burris says, “something more deliberate, sophisticated.”

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

“Choose a lane and go at full gallop.”

Customers are looking for looks that are customized, put together, and personalized. Instead of excessive embellishments, Burris said, they are looking for something with “no less impact, but more deliberate and elevated.”

This year, that impact is less about intricate embellishments and more about the materials. Burris describes one The shiny straw hat she designed this year Lurex (a metallic, shiny fabric) is woven into it. She’s emphasizing bold shapes, but with sophisticated, simple trim, like a foxglove with couture featherwork, or a voluminous fringe with restrained metallic ribbon.

“When you get to the track, you want to look thoughtful,” says Burris. “That’s the thing that will really surprise you; the details really matter.”

The same thing applies to men’s clothing also.

“For those wearing masculine styles, you don’t want to look like you’re auditioning for a Mint Julep commercial,” Rassi said. “A strong statement is enough. That could be a sharp suit in a light fabric but in a striking colour. We’re also seeing in high fashion, men wearing more collarless cuts with popped collars or funnel necks.”

And speaking of friends…

brooches for men’s clothing

For men? Try a brooch!

“On the Oscars carpet, it seemed like every single person had a brooch, and if you didn’t have a brooch, you were underdressed,” Rassi said. “Guys, take a look at Pedro Pascal’s Oscar Chanel outfit with the feather brooch. Take a good look at it and get to work.”

Pedro Pascal in a custom Chanel ensemble with a feathered floral brooch at the 2026 Oscars. (Julian Hamilton/Getty Images)

Floral for spring… but *really* phenomenal

Flowers are to the Kentucky Derby what sneakers are to basketball: essential beauty.

Several people we spoke to joked about the classic line from “The Devil Wears Prada”: “Floral? For spring? Groundbreaking.”

But, Rassi says there are ways to make a floral look truly unique.

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

Anne Hathaway and Anna Wintour at the 2026 Oscars. Hathaway wore a Valentino black floral gown by Alessandro Michele (Patrick T. Fallon/AFP via Getty Images)

“The flowers are always there,” says Burris. “We teamed up with a fourth-generation flower workshop in the heart of New York City’s apparel hub, M&S Schmallberg, which is a reminder that getting ready for the Derby is a great way to support local crafts.

“We work with local artisans and craft workshops, whether it’s custom dyed feathers or beautiful silk flowers made in a particular fabric and type of flower. It’s a great way to support local artisans and small businesses.”

Kennedy-Corps American preparations: skirt suit, pillbox hat, JFK Jr.

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

“The reference point for the audience will be the revival of ‘Love Story,'” says Rassi, referencing the 2026 hit Netflix series about JFK Jr. and Carolyn Bessette. “It’s that great preparation, American classics. A little country club, a little old money, a little miss came up 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 suit

Rope Jackie O. The vibe suggests a skirt suit and a pretty silk scarf.

“We’re seeing a lot of skirt suits,” says Rassi. “From Chanel to Christian Dior, they were definitely prominent on the runways. They’re emblematic of the moment.”

How to make it yours: Ropes suggests a short jacket with a pretty, sharp pencil skirt – “it could be tweed, it could be floral” – or a dropped waist skirt for something unique. “In the channel’s most recent high-profile show, we saw the skirt suit take a completely new look,” says Rassi.

For a more ’90s look, the raw CBK look: “Choose a slip dress, wrap a crew neck around your shoulders and wear loafers. Very minimalist Calvin Klein.”

old hats

For men, achieve this classic American look with a newsboy flat cap à la JFK Jr.

For women, pillbox hats are back!

“What I would personally wear is a pillbox,” Rassi said. “Not only is it the biggest trend for the Kentucky Derby, but it was also huge on the runway. Jennifer Lawrence was seen Taking your kid on a trip to the pillbox.”

US 250 topic?

Woodford Reserve has a specially designed Kentucky Derby-edition bottle featuring a red-white-and-blue motif that celebrates the “American 250”.

Burris said, “It will be interesting to see if more red, blue and ivory colors are woven into Churchill’s fashion.” He said they are seeing a significant increase in customer requests this year.