2026 Kentucky Derby outfits and hats that you can style all season long
From statement hats to standout suits, a Kentucky Derby outfit is all about dressing like you mean it, and this year’s Derby fashion trends are off to the races.
TODAY style correspondent Zanna Roberts Rassi spoke with Jenna & Sheinelle and TODAY.com about what to expect for styles of the season.
“These looks are the kind of little things that you can wear for the Derby, but also are going to see you the entire season through.”
You don’t have to be at Churchill Downs to dress in style, so read on for some advice on what to wear for your garden party.
And be sure to watch the 2026 Kentucky Derby live Saturday, May 2, on NBC and streaming on Peacock.
Dress like a Kennedy
“If you really want to nail your Derby look … just think Kennedys,” Rassi says.
The popularity of the TV show “Love Story,” about John F. Kennedy Jr. and Carolyn Bessette Kennedy, has inspired a sense of nostalgia around American classics. Rassi says to embrace the country-club and old-money style in your Derby look.
“Channel Jackie O in her elegant, lady-like accessories,” she says.
Pillbox hats, closed-toed shoes and top handle bags are all in for this season, and help elevate the Derby outfit. For a matching couple’s look, try out pale blue suit and dress pairing. “Blue is definitely the color of the season,” Rassi says.
For men’s attire, “you can’t go wrong with a seersucker suit when it comes to the Derby. This will be the suit that keeps on giving through the summer events and beyond.”
Lean into chocolate brown
The spring season usually brings light pastels into the catalogue, but this year a shocking new color is trending: brown.
“The trend you didn’t expect and will see everywhere? Chocolate brown! Make way pastels — there’s a new cool-girl color in town,” Rassi says.
Alongside the typical Derby styles of florals, polka dots and prints, chocolate brown is being added to the mix. The fascinator, aka the decorative hat attached by clips or a headband, is a distinctive Derby style and a perfect place to add a pop of color to your brown Derby outfit.
“Cool color. Cool fabric. Cool sneaks. These two are ready to take on the track, and the town!”
Get yourself a 3-piece suit
Rassi explains that “a three piece summer set is the moment” for the Derby and into summer.
Try a monochromatic matching set in your favorite color to embrace a bold new look. Apart from the Derby, you can wear each piece individually in the summer months. A well-fitted, matching outfit is also a staple to have in your closet.
“You need a three-piece suit in your arsenal this season,” Rassi says.
Try color blocking — but do it properly
Color blocking is a classic way to bring in personality — but juggling too many different colors and patterns can be tricky. Rassi’s pro tip? Stick with two or three main colors and ditch the prints.
“Color blocking works because the eye reads clear sections of color,” she says.
If you want to be adventurous, try unique colors that are not commonly used together.
“Double points for making them quirky color combinations that feel slightly ‘wrong’ at first glance — then suddenly genius.”
This story first appeared on TODAY.com. More from TODAY:
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