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

If you purchase an independently reviewed product or service through a link on our website, WWD may receive an affiliate commission. 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

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