What to Wear to a Kentucky Derby Party

One of my favorite fashion events of the year is coming up soon-the Kentucky Derby! I’ve never actually been to the Derby before, but it’s on my bucket list. In the meantime, I love a good excuse to wear a favorite sundress and a floppy hat at a Kentucky Derby Party. Due to COVID, I haven’t been to a Kentucky Derby party since 2019, when I went to a really fun event in downtown Raleigh with some friends.  Although I will be waiting until next year to resume the usual Derby Day festivities, I realize many people are starting to gather again. So, I’m sharing some inspiration on what to wear to a Kentucky Derby party. I’ve rounded up a handful of options. Keep reading for preppy dresses, seersucker, and hats galore!

FYI: The 2021 Kentucky Derby is on May 1.

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Lilly Pulitzer for the Kentucky Derby

What to Wear to a Kentucky Derby Party Lilly Pulitzer
(Photo by Amelia Cassar Photography)

You honestly can’t go wrong with throwing on a classic Lilly Pulitzer shift for a Kentucky Derby Party. In the picture above, I am wearing the Mila Shift in On Parade. This was my one clothing purchase from the January 2019 Lilly After Party Sale. Although this particular shift is no longer available from the Lilly website, there’s still plenty of great options. These are my top picks for Kentucky Derby 2021 that are currently available from Lilly:

Tabby Shift Dress in Bunny Business. Easter may have already passed, but this adorable bunny print in a classic shift dress style is perfect to wear all spring and summer.

Clarise Shift Dress in Periwinkle Sand Dollar Eyelet. The Clarise Shift is one of my favorite dresses currently available on the Lilly website. I’m a sucker for anything with an eyelet detail, and I love the bow detail in the front. In addition, the periwinkle color is so pretty and screams “spring.”

Tisbury Shift Dress in True Navy. The Tisbury Shift is a classic style that Lilly Pulitzer has kept around for a few years. It’s very similar style to a pink seersucker Lilly dress I’ve had for nine years now. There’s sweet ruffle detail around the neckline and chest, and the navy color it’s currently available in is very versatile.

Mila Shift Dress in Lilly’s Favorite Things. The Lilly Pulitzer Mila Shift is back in new prints this season. Lilly’s Favorite Things is one of my favorite prints. I actually have all the pajama pieces in this print.

Callista High Collar Shift Dress in True Navy. The Callista is another classic navy shift dress from Lilly Pulitzer. I love the white appliqué detail down the front.

Trisha Shirt Dress in Spotted on Worth. This is such a classic Lilly print, and I love the tie around the waist.


Shop all Lilly Pulitzer dresses here.

More Kentucky Derby Party Dress Ideas

Although Lilly Pulitzer is always a great option for a Kentucky Derby party, there’s some amazing dresses from some of my other favorite brands that would be perfect too! Here are a few I’m especially loving:

Draper James Taylor Smocked Dress in Orange Blossom. I’m obsessed with the new Orange Blossom print by Draper James, Reese Witherspoon’s lifestyle brand. This bright and cheery dress is a great option for anyone looking for what to wear to a Kentucky Derby Party.

Draper James Reba Wrap Dress in Pink Seersucker. You can’t go wrong with pink seersucker for a Kentucky Derby party, or any spring gathering for that matter! This same style dress is also available in white seersucker, which would look great paired with a colorful hat.

Vineyard Vines Kentucky Derby Floral Gingham Side-Tie Dress. Vineyard Vines makes official Kentucky Derby dresses each year, so this darling floral gingham print dress is an obvious choice for a Derby Party!

Southern Tide Erika Performance Seersucker Shift Dress. This classic seersucker dress from Southern Tide has a removable sash and moisture-wicking performance fabric. In addition, the fabric is UPF 50+. This would be an especially great option if you are going to be outdoors.

Southern Tide Sammi Gingham Performance Wrap Dress. Gingham is a preppy staple that is always in style, and I love the coral color of this dress from Southern Tide. Wrap dresses appear to be especially popular this spring. The ruffle detail on this one is so pretty too!


Don’t Forget Your Hat!

Kentucky Derby Party Hat

Honestly, the addition of a cute floppy hat is what distinguishes a Kentucky Derby party outfit from any other occasion involving a preppy sundress. The hat I’m wearing in the above photo by Amelia Cassar Photography was actually a Lilly Pulitzer Gift with Purchase years ago. But here are a few options I found that would be a great complement to your Kentucky Derby party dress this year:

J.Crew Textured Summer Straw Hat
J.Crew Factory Textured Summer Straw Hat (A more budget-friendly option)

Thanks so much for reading! If you enjoyed this post, you can go to the homepage and subscribe to my blog. In addition, you can follow me on Instagram, Facebook, or Twitter. For even more preppy style inspiration, you can subscribe to my e-newsletter, and get a bonus guide on how to score some of my favorite brands for less!

Do you have plans for the Kentucky Derby this year? If so, have you decided what you’re wearing?

-xoxo Liz

PS. Here’s a catalog of the dresses  I mentioned in this post. Click on any picture, and it will take you directly to the retailer’s website:

Hey Y'all!

I'm Liz- and I'm here to inspire you to embrace the simple joys in life and encourage you to be your authentic self!

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  1. Annaliese wrote:

    It’s on my bucket list to go to the Derby someday! I have been to Churchill Downs before (a couple weeks after) and it was INCREDIBLE! I don’t have plans yet but hopefully I’ll go to a Derby party. 🙂

    xoxo A

    Posted 4.18.19 Reply