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Your Ultimate Kentucky Derby Shopping Guide 2026
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.
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). Rassi’s comprehensive list of Kentucky Derby dressing tips is available now on the annual horse race’s site, but she 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
Price upon publish date of this article: $700
Dolce & Gabbana Foiled Organzine Turban
Price upon publish date of this article: $825
San Diego Hat Co. Polka Dot Boater
Price upon publish date of this article: $80
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 latest spring show as a reference point).
Theia Vada Taffeta Shirtdress
Price upon publish date of this article: $645
Ralph Lauren Cape Georgette Dress
Price upon publish date of this article: $144.99
Petal & Pup Butterfields Strapless Minidress
Price upon publish date of this article: $89
“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.
Lands’ End Squall Packable Waterproof Raincoat
Price upon publish date of this article: $159.95
Damson Madder Matilda Gingham Hooded Raincoat
Price upon publish date of this article: $280
Satinior Women’s Rain Bonnet, Set of 6
Price upon publish date of this article: $8.99
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.”
Castaner Azulon Careen Wedge Heel
Price upon publish date of this article: $150
Cole Haan Cloudfeel Asbury Mary Jane Ballet Flat
Price upon publish date of this article: $170
Aerosoles Women’s Dress Platform Heel
Price upon publish date of this article: $150
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
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
Time is of the essence: both when it comes to Thoroughbred racing and snagging this Bulova bestseller before the Kentucky Derby.
Until April 31, you can get an extra 10 percent off your Bulova order with the code WWD10 at checkout.
Price upon publish date of this article: $396
Coach Outlet Country Club Floral Print Silk Skinny Scarf
”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
Gucci Half Horsebit Necklace
Been chomping at the bit for your chance to own Gucci jewelry? Start here.
Price upon publish date of this article: $2,000
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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).
Source: Shop – wwd.com
