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What to Wear to the Kentucky Derby, According to a Style Expert and Longtime Attendee

We spoke with Zanna Roberts Rassi — Milk Makeup co-founder, entertainment journalist, and guest editor of the official 2026 Kentucky Derby Style Guide — to demystify the iconic event's dress code.

By Stacia Datskovska Plus Icon

Stacia Datskovska

Senior Commerce Writer for WWD

Recent Articles by Stacia Datskovska

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April 22, 2026, 3:25pm

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woman wearing an intricate lace dress and holding a bag with horse applique on it; woman and man posing at the kentucky derby; what to wear to the kentucky derby 2026

Courtesy Andrew Kung Group

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The Masters came and went, and now another historic event with a famously hard-to-crack dress code is upon us: the Kentucky Derby, of course, which is set to take place on Saturday, May 2, at the horse racing complex Churchill Downs in Louisville, Kentucky. If you’re planning on skipping the more casual infield celebrations and heading straight for the first-turn reserved seating that weekend, you are probably well aware that a lot is expected from you in the fashion sense. Grabbing a fancy hat and staying away from umbrellas (thank us later) should be muscle memory, but it’s tougher to crack the grand happening’s more hush-hush dressing requirements.

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To help simplify your packing journey and fill you in on exactly what to wear to the Kentucky Derby, we tapped the aid of Zanna Roberts Rassi — Milk Makeup co-founder, Today Show style correspondent, and guest editor of the official 2026 Kentucky Derby Style Guide. She’s held this latter position for multiple years now and is a veritable veteran where Derby attendance is concerned; this year, Rassi will be providing Derby coverage live on NBC, both on Kentucky Oaks and Derby Day. Cable cutters can catch the broadcast with a DirecTV trial or Peacock. Her comprehensive list of Kentucky Derby dressing tips is available now on the annual horse race’s site, but Rassi sat down with WWD to boil down the generous advice to a handful of indispensable points that will get you ready for the big, mint julep–fueled day in no time.

Zanna Roberts Rassi attends the 150th Kentucky Derby at Churchill Downs on May 4, 2024. Courtesy Daniel Boczarski/Getty Images

First off? Hats, hats, and more hats. It doesn’t take being a Churchill Downs Millionaires Row mainstay to realize that you can’t show up to the track without a head covering: a rule that’s applicable particularly to women. Per Rassi, this accessory should serve as the focal point of your outfit — drawing in the eye and setting the stage for the look’s overarching aesthetic.

”Instead of shopping your outfit and then trying to figure out the hat as an afterthought, start with the hat,” Rassi tells WWD. “Are you going for the pillbox? For something that’s big, with feathers and florals? Decide on that first and let everything else slot in after.”

Regarding the hat designs to click “add to cart” on, Rassi suggests taking a page from recent runway presentations. She mentions seeing pillbox styles at many junctions, “from Altuzarra to Chanel.” So too is the structured-and-whimsical a safe bet for 2026, with details like veils and compositions like straw merging both worlds while preserving the perfection of your blowout. Another stellar option is scull caps. The just-passed Coachella provided ample inspiration for styling their crochet versions, but Rassi insists on swapping this material for something more formalized and Derby-aligned while keeping the silhouette intact. (Better yet if you can find a low-profile cap adorned with tasteful accents like bows and brooches, or else one that takes on the identity of an oh-so-chic turban.)

“Start with the hat.”

– Zanna Roberts Rassi

Lele Sadoughi Navy Berry Loop Pillbox Hat

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Dolce & Gabbana Foiled Organzine Turban

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San Diego Hat Co. Polka Dot Boater

$80

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Clearly, some Kentucky Derby hat prices are far from a walk in the park for your wallet, but Rassi believes the staple is worth investing in if “that is your moment, and then maybe… you go and get a dress from Mango.” After all, if you choose your hat based on the season’s most prominent trends, you’ll be able to wear it beyond May 2 — to brunches, bachelorette parties, fundraiser galas, weekend bed-and-breakfast escapes, and everything in between.

Attendees wear colorful hats at Churchill Downs on May 2, 2025. Courtesy Leandro Lozada/Getty Images

In Rassi’s opinion, the Kentucky Derby’s sartorial conventions ”sit somewhere between a garden party, a wedding, and a fashion event.” The guide she edited also has an art-meets-style through line, winking at the theme of the 2026 Met Gala, which will happen just days after the last horse at Churchill Downs goes back to its barn. Fittingly, Rassi encourages thinking artistically about the “joyful daytime couture” you’re going to wear and letting your personality shine through the occasionwear.

In practical terms, this might mean cosigning a quirky, unexpected color or color combination. Try a ”purple, lime, cobalt, and chartreuse,” according to Rassi, which is “not normal for the Derby, but so relevant.” She continues: “ Rather than pushing the silhouette, push the volume on the color. It doesn’t have to be chaotic.” Just remember to anchor your ensemble with a base shade and color-block from there (Rassi uses Prada’s late s t spring show as a reference point).

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Ralph Lauren Cape Georgette Dress

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“Push the volume on the color.”

Selma Blair, Simone Biles photographed at the Derby on May 3, 2025, in Louisville, Kentucky. Courtesy Jeff Schear, Daniel Boczarski/Getty Images

Popping open an umbrella while viewing the proceedings at the open-air grandstands would completely block the view of the attendees behind you, which is precisely why this rainy-day must-have is banned by organizers. A smart solution? Making your rain protection wearable, obviously. “Luckily, windbreakers are very ‘in’ right now, and so are anoraks with drawstring waists and hoods,” says Rassi. “ Because the trench is lovely, but it’s not very practical if you want something over your head.” The runways have once again delivered in this department, as fashion houses from Lacoste to Tory Burch turned up the heat on the sporty attire with eye-popping shades, glossy fabrics, contrast zippers, and other skillful touches in their spring collections. Take these design directions to heart… or alternatively stick to more timeless outerwear, marked by subdued colorways and classy prints.

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Damson Madder Matilda Gingham Hooded Raincoat

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Satinior Women’s Rain Bonnet, Set of 6

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Another aspect of the Kentucky Derby that eludes a lot of newbies — before they learn the hard way — is just how much walking is involved. ”There is nothing worse than being trapped in your shoes. It’s going to make your day so miserable,” Rassi shares. “The steps are in the tens of thousands because you first want to do the betting, then you go to the course, then you walk to get food.” Churchill Downs sits on over 140 acres, so you’re guaranteed to be more worn out than Sovereignty on the night of May 3, 2025, when all is said and done.

The secret remedy to such fatigue is, as it turns out, not so secret and simply revolves around wearing footwear that balances elevated looks with comfort. “ Flats are back, and we’re very happy about that,” Rassi tells us. “Wedges are also great, but you don’t have to go with ones that are too high — two, three inches only. Also block heels: We’re seeing a lot of those.”

A big no-no? Flip-flops, which Rassi admits are majorly en vogue but begs Kentucky Derby guests to steer clear of. To mimic flip-flops’ breathability while successfully avoiding blisters, opt for mule slides, mule heels, or Mary Janes instead (essentially, anything that you won’t end up carrying in your hand post-race, which is “not a good look,” as Rassi puts it).

A Derby guest fixes her hat — and holds her shoes — while on the way to the infield at the 2016 Kentucky Derby. To quote Rassi, “not a good look.” Courtesy Michael Noble Jr./Getty Images

One of her most crucial pieces of advice, shoe-wise, is to test out your just-bought pair for at least two hours before the day of the Derby. “Walk around the office in it, walk around the house in it,” Rassi says, and only then pack it into your carry-on. Indeed, your only surprise of the weekend should be betting on a winning horse. Also: Bring more Band-Aids (Hydro Seal gets a special shoutout from Rassi) than you think you’ll need. Again, you’re welcome.

“There is nothing worse than being trapped in your shoes.”

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Cole Haan Cloudfeel Asbury Mary Jane Ballet Flat

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Aerosoles Women’s Dress Platform Heel

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Craving even more style inspo for “The Most Exciting Two Minutes in Sports”? Below, some additional outfit ideas courtesy of our editors, from all-pink looks for the Oaks to Millionaires Row–worthy stylings.

Sign up for WWD Shop‘s newsletter to get the scoop on the best in beauty and style with in-depth reviews of exciting new releases and buyer’s guides to find the products you need to try ASAP.

Kentucky Derby Outfit 1: The Gen Z First-Timer

Marina Moscone Mini Dress With Floral Appliqué ($2,990), Karen Millen Quil Detail Headband Fascinator ($199), Cult Gaia The Backgammon Clutch ($798), Caravelle by Bulova Vintage Classic Watch ($140), Clarks Jaylan Sol Heel ($84) Courtesy Manufacturers

Kentucky Derby Outfit 2: The Infield Avoider

Hill House Home The Blythe Bow Dress ($229), Born to Roam London Pillbox Hat ($185), Coach Outlet Teri Shoulder Bag ($199), Breda Dalmata Time Ring ($150), Le Specs Outta Love Sunglasses ($75), Naturalizer x June Ambrose Nova Dress Sandal ($275) Courtesy Manufacturers

Kentucky Derby Outfit 3: The Lover of Lillies and Fillies

Milly Bryn Tweed Top ($375), Milly Briar Tweed Mini Skirt ($325), Lilly Pulitzer Shade Seeker Hat ($68), Betsey Johnson The Mane Event Shoulder Bag ($98), Jennifer Behr Demetria Earrings ($350), Anthropologie Matisse Exclusive Embroidered Platform Heeled Sandal ($68) Courtesy Manufacturers

Even More Derby-Approved Accessories to Shop Before May

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”There’s so much pink at the moment,” Rassi says. “Every shade of the spectrum is out there.” Use that to your advantage, and say “yes” to the hue with Coach Outlet’s top-selling skinny scarf.

Price upon publish date of this article: $78

Dolce & Gabbana Long Tulle Gloves

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“Think Jackie O — a little ‘Love Story’ influence!!” Rassi offers.

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Why Trust WWD

Since 1910, WWD — often referred to as “the fashion bible” — has been the leading industry voice of authority for senior executives in the global women’s and men’s fashion, retail and beauty communities, while also informing the consumer media that cover the market. Today, WWD’s breaking news and trend coverage continues to be a trustworthy resource for both fashion insiders and consumers alike. Our shopping editors continue to uphold WWD’s editorial standards and values with quality, expert-backed product selections. Learn more about us here.

Meet the Author

Stacia Datskovska is a Senior Commerce Writer at WWD. Previously, she worked at ELLE DECOR as an assistant digital editor, covering all things luxury, culture, and lifestyle through a design lens. Her bylines over the past five years have appeared in USA Today, Baltimore Sun, Teen Vogue, Boston Globe, Food & Wine, and more. Prior to joining ELLE DECOR, Datskovska learned the ins and outs of e-commerce at Mashable, where she tested products, covered tentpole sales events, and curated gift guide roundups. She graduated from NYU with a bachelor’s degree in journalism and international relations. Datskovska regularly reports on seasonal style trends and doles out occasion-specific fashion suggestions that are easy to follow (not to mention shop online).

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What to Wear to the Kentucky Derby, According to a Style Expert and Longtime Attendee

Recent Articles by Stacia Datskovska

In this article

View More

Your Ultimate Kentucky Derby Shopping Guide 2026

Lele Sadoughi Navy Berry Loop Pillbox Hat

Dolce & Gabbana Foiled Organzine Turban

San Diego Hat Co. Polka Dot Boater

Theia Vada Taffeta Shirtdress

Ralph Lauren Cape Georgette Dress

Petal & Pup Butterfields Strapless Minidress

Lands’ End Squall Packable Waterproof Raincoat

Damson Madder Matilda Gingham Hooded Raincoat

Satinior Women’s Rain Bonnet, Set of 6

Castaner Azulon Careen Wedge Heel

Cole Haan Cloudfeel Asbury Mary Jane Ballet Flat

Aerosoles Women’s Dress Platform Heel

Bulova Super Seville Mini Watch

Coach Outlet Country Club Floral Print Silk Skinny Scarf

Dolce & Gabbana Long Tulle Gloves

Gucci Half Horsebit Necklace

Related Articles

Lele Sadoughi Navy Berry Loop Pillbox Hat

Dolce & Gabbana Foiled Organzine Turban

San Diego Hat Co. Polka Dot Boater

Theia Vada Taffeta Shirtdress

Ralph Lauren Cape Georgette Dress

Petal & Pup Butterfields Strapless Minidress

Lands’ End Squall Packable Waterproof Raincoat

Damson Madder Matilda Gingham Hooded Raincoat

Satinior Women’s Rain Bonnet, Set of 6

Castaner Azulon Careen Wedge Heel

Cole Haan Cloudfeel Asbury Mary Jane Ballet Flat

Aerosoles Women’s Dress Platform Heel

Kentucky Derby Outfit 1: The Gen Z First-Timer

Kentucky Derby Outfit 2: The Infield Avoider

Kentucky Derby Outfit 3: The Lover of Lillies and Fillies

Even More Derby-Approved Accessories to Shop Before May

Bulova Super Seville Mini Watch

Coach Outlet Country Club Floral Print Silk Skinny Scarf

Dolce & Gabbana Long Tulle Gloves

Gucci Half Horsebit Necklace

Why Trust WWD

Meet the Author

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