With the Kentucky Derby, Preakness Stakes, and Belmont Stakes fast approaching, you may be at a complete loss at what to wear. Same, girl, SAME. It’s not every day you get invited to Churchill Downs (or a Derby-inspired bash) after all. We’re decoding exactly what to wear — from the fancy headwear to your pastel-hued frock and Derby-approved steppers — for the season’s preppiest fashion extravaganza. Scroll through for four Triple Crown-worthy #OOTDs that will have you winning at the races, whether your horse comes in first or not.
Say “yes” to the Derby dress. Because you’ll want all eyes on the dress, switch out the OTT hats and fascinators for a Blair Waldorf-approved silk headband and classic Swarovski crystal daisy studs. We’re loving this updated woven rattan satchel that’s just roomy enough to tote the essentials. Get around-the-clock comfort with a pair of M.Gemi’s sensible metallic gold low-heeled sandals that won’t sink into the grass. Steer clear of a wardrobe malfunction with the help of Dress Downs, adhesive garment weights designed to keep your skirt down and head high when the wind blows.
Clockwise from top left: Frances Valentine Elizabeth Cole Bower Daisy Earrings in White ($68), Eugenia Kim Brianna ($175), Kate Spade New York Bloom Street Sam Rattan Satchel ($398), Dress Downs Garment Weight ($12), M. Gemi The Allegra ($228), Gal Meets Glam Collection Lillian ($198)
Embrace color in a major way, starting with some rainbow stripe trousers and coordinating lilac geometric block heels. For accessories, allow this charming jeweled clutch to add sparkle to your look alongside a pair of beaded tassel earrings. Proceed to keep cool in hot and sticky conditions this summer with a flouncy one-shoulder top and a wide-brim tassel-adorned wicker hat that’ll be non-negotiable when soaking up rays from the stands.
Clockwise from top left: Ganni Wilkie Ruffled Striped Silk Cotton-Blend Seersucker Top ($315), BaubleBar Granita Beaded Tassel Earrings ($38), Scotch & Soda Wide Brim Wicker Hat ($115), Ann Howell Bullard Jeweled Clutch ($250), Katy Perry Collections The Margot ($100), Topshop Rainbow Slouch Trousers ($75)
Test-Drive a Jumpsuit
Boho babes, rejoice! With the right add-ons, even the most Colorado Desert-bound jumpsuit can look at home on the racetrack. Offset this Rebecca Minkoff striped stunner with eye-catching accessories — like this square-shaped cautionary orange crossbody bag and a pair of J.Crew’s signature Ratti Rio floral sandals. Simple brass moon dancer earrings will go a long way, especially when teamed with a spectator-worthy Panama hat. Last, but not least, allow this ceaselessly chic hooded khaki trench from the Hunter x Target collab to keep you dry should you get caught in a spontaneous downpour.
Clockwise from top left: Modern Weaving Tiny Moon Dancer Earrings ($120), Hunter x Target Hooded Trench Coat in Khaki ($45), Sensi Studio Frayed Woven Straw Boater Hat With Adjustable Band ($195), Rebecca Minkoff Marley Jumpsuit ($228), Henri Bendel West 57th Square Crossbody ($198), J.Crew Wrap-Around Heels in Ratti Rio Floral ($248)
Whether you’re observing from the sidelines or sipping rosé at the after-after party, this #girlboss-infused millennial pink suit is game for it all. Keep the pretty ‘n’ pink theme going with a pair of extra AF crystal embellished sunnies and one of Kayu’s hand-painted woven straw clutches. Embrace your inner Hollywood starlet with a French Riviera-inspired boater hat and classy scallop-trimmed block heel sandals. To ensure that you’re selfie-ready, top off your look with a true red lipstick. C’est si facile!
Clockwise from top left: Scotch & Soda Double Breasted Herringbone Blazer ($225), Kitsch Ribbon Straw Boater Hat ($26), Alice + Olivia Madison Floral Sunglasses ($525), Scotch & Soda Tailored Herringbone Pants ($148), Loeffler Randall EMI Block Heel Sandal ($325), KAYU Florence Clutch ($225), Troi Ollivierre Lipstick ($28)
Which of these Derby-inspired getups will you be rocking at the races? Follow us on Pinterest for more styling inspo for the season!
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