What to Wear to the Kentucky Derby

If you aren’t too worn out from the Oaks, then it’s time to get ready for the Kentucky Derby, the “fastest two minutes in sports!” Always held the first weekend in May, it’s the one day at Churchill Downs that is like no other you’ll ever experience with 165,000 of your closest horse-loving aficionados. When we first moved to Louisville, it was at the top of my to-do list and although it’s been checked off, it’s an event that becomes a tradition. But the big question I had, was “what to wear to Kentucky Derby day?”

I’ve realized the key to a great look at the Kentucky Derby is: comfort, comfort, cuteness. And yes, in that order. This is not a day that you actually want to sacrifice style for comfort (and it’s rare that those words will pass my lips). The day starts before noon, parking is more than a stone’s throw from the Twin Spires of Churchill Downs, socializing & fashion-scoping is high on the agenda so you’ll be walking around most of the day, and somebody’s drink somewhere on you is just part of the experience!

Comfort may be key, but nobody is foregoing fashion when deciding what to wear to Kentucky Derby. Cute comfortable shoes, like these with a cork wedge sole, and a printed dress to hide mint julep stains are ideal. Although big floppy hats are a Kentucky Derby tradition, they are a pain in the you-know-what. You bump everyone, you can’t see, and by the end of the day, they are just plain uncomfortable. So, I prefer fascinators or small hats, but whatever you choose, whatever you wear, & wherever you are… Derby On!


how to know what to wear to kentucky derby

hat: Brooks Brothers / dress: Milly / purse: Henri Bendel / shoes: Ann Taylor

Let us know – is the Kentucky Derby on your radar? Do you watch it on tv or have you attended?

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  • Rebecca Mill

    Comfort is DEFINITELY key. I just got home from Foxfield which is a steeplechase here in Virginia and my knees are killing me! It is SO necessary to choose a good pair of choose for the day!

  • http://www.popcosmo.com/ PopCosmo

    Virginia gals know how to party! Hope you had a blast and that your knees are recovering!!!

  • meghan silva

    Haven’t been to a Derby before however I have seen a few on T.V. love the look you chose out.

    Meghan Silva’s Blog

  • http://www.popcosmo.com/ PopCosmo

    Thank you! We used to watch it on TV before moving here and I always dreamed of going. So glad that I finally made it :) If you ever have the chance, it’s a must-do!!! Just an absolute party and a full day of fun – what’s not to love?

  • http://twitter.com/VogueAndHeels Vogue and Heels

    Love this style! That dress is gorgeous.



  • Spashionista Alicia Searcy

    I would love to go sometime and I’ve been meaning to check on wheelchair accessibility for the event. I just never remember to do that until the week before the race LOL! I love the race day outfit you’ve styled. I think black and pink are a very chic color combination :-)

    Spashionista (Alicia)

  • http://www.popcosmo.com/ PopCosmo

    I think tix would definitely have to be bought in advance… but it’s something to consider! Here’s a link that might help: http://www.churchilldowns.com/tickets/handicapped-accessible-seating. The crowds are, well, crowds! I’d suggest Oaks Day or even Thursday before the Derby for a little tamer crowd! Hope you can make it one day!

  • http://www.popcosmo.com/ PopCosmo

    Thanks so much, it’s definitely on our wish-list!