This Saturday, 20 of the world’s fastest thoroughbreds will make the 151st run for the roses—but our eyes will be fixed firmly on the fashion.
Whether you’re hosting a Derby Day party or attending the event in person, you’ve likely had your outfit planned, steamed, and hanging in your closet for the world’s longest two minutes—or far longer. But, if you just snagged an invitation to celebrate this year’s Kentucky Derby, you may be in need of some last-minute inspiration to help you saddle up in time for the party.
Our editors have put together five delightful Derby-inspired looks to help you shine, whether it’s under the Kentucky sun or your own roof. Whatever your mood this Derby Day, we have a look for you.
If You’re Ready to Run for the Roses:
It wouldn’t be springtime in the south without a dose of pink flowered frocks, and there’s no better outfit than this to celebrate horse racing’s most fashionable event.
This rosette-skirted strapless mini is fresh and flirty, with a low-cut back and three-dimensional flower appliqués to emphasize the floral theme. Continuing the floral motif, the cotton-candy pink purse features a vintage-inspired faux pearl handle and wide-brimmed fascinator hat in a similar shade reinforces the classic aesthetic.
With the addition of these satin stilettos, accented with oversized rosettes on the toe, and flower-printed lace gloves with miniature bows at the cuffs, the look is as frothy and refreshing as a strawberry milkshake.
If You Want to Channel the Royal Ascot:
Girls who’ve swooned over Audrey Hepburn’s transformation from Eliza Doolittle the flower girl to the pinnacle of London society in My Fair Lady—this one is for you!
Beginning with a simple corseted lace maxi dress with half-hidden embroidery on each tier, this outfit is anything but understated. Adding a dash of Hepburn’s black-and-white signature, a two-tone feather fascinator hat pairs perfectly with Dior’s iconic j’adior slingback pumps for a modern touch.
It’s not Audrey’s ruffled parasol, but this sleek patent leather clutch with a bold flash of gold hardware is the perfect way to complete the ensemble for a delightfully modern take on one of classic Hollywood’s most iconic wardrobe moments.
If You’re Already Mixing Up a Julep:
You don’t really care who wins the race, because you’re here for the party! Whether you’re traipsing around the track with your tribe or lounging on the couch with your besties, you’re all about the food…and the fashion!
If you’re ready for your outfit to be the highlight of the day, start with this eye-catching asymmetrical mini dress in a soft pastel green, then go wild with accessories. For a playful pop of silver every time you kick up your heels, try these Cinderella-style pumps—after all, who needs red soles when you can have sparkles?
Keep on working your maximalist magic by adding a rhinestone-embellished clear acrylic handbag—is it giving ice cube vibes, or are we just thirsty? Of course, a Derby Day ensemble wouldn’t be complete without channeling a bit of old money energy. (This iconic mother-of-pearl necklace should fit the bill…) Add an oversized bow fascinator (complete with feathers and pearls) for a touch of whimsy to make you look like a surefire winner!
If You’re On Your Way to Make Your Bets:
You might be all business, but that doesn’t mean you aren’t ready to party! You can do both with effortless elegance in this stunning ensemble that combines the best of sartorialism with the free-spirited elegance of the American south.
This full-skirted blazer dress features puffed sleeves, statement gold buttons, and a delightful jacquard print which helps wearers bridge business and pleasure. With the addition of delicate satin stilettos trimmed with oversized bows and a wide-brimmed hat featuring the same, you can embrace your femininity even in a sea of stallions.
To keep things on track, consider a vintage cocktail watch (bonus points if it it’s a Longines—they sponsor the Derby!) and a leather clutch that’s sleek and dainty yet large enough to carry your betting essentials…and the cash if you win!
If You’re Ready for Your Photo Finish:
Ready for the winner’s circle? This outfit has you covered. We’re channeling the The Black Stallion with this black-on-black ensemble and, while it’s certainly not the most springy thing we’ve seen, it’s perfect for those girls born to stand out!
Inspired by classic riding jackets, this button-up minidress features a dramatic three-dimensional hem covered in pleats and rosettes. It’s perfectly complemented by a pair of black mesh pumps festooned with gigantic bows.
Hinting more overtly at the Derby Day theme, we complete the outfit with a mini saddle bag—also black—and an oversized flower fascinator hat. If you haven’t already gathered, this winner’s circle-worthy look proves that more can, in fact, be more.
Final Thoughts
We’re always grateful for a good excuse to go all-out with our outfits, and the Kentucky Derby is just that. Whether or not you’re hitting the racetrack this weekend, save this advice for the next time you need an outfit that offers a little extra. After all, the Met Gala is just around the corner…