Hey y’all-hope you’re having a great week! One of my favorite fashion events of the year is coming up in just a little over two weeks-the Kentucky Derby! I’ve never actually been to the Derby before, and I honestly don’t even go to a Kentucky Derby party every year. But I love any excuse to wear a favorite sundress and a floppy hat. One of these years I’m actually going to host a Kentucky Derby party, but this year I’m looking forward to going to one in downtown Raleigh with a friend. Anyways, today I wanted to give y’all 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!

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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. I am wearing the Mila Shift in On Parade, which was my one clothing purchase from the January 2019 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 2019 that are currently available from Lilly:

Romee Wrap Dress in “Lion Around” (This might be my favorite dress currently on the Lilly website!)
Margot Swing Dress in “Multi Cheek to Cheek” (Love this patchwork print, and this dress is less expensive than most Lilly dresses.)
Melani Shift Dress in “Coastal Blue Fancy Feet” (Love the lace detail down the front of this shift.)
Maya Shift Dress (This dress is white eyelet at the top, and seersucker from the waist down. Comes in both pink and blue seersucker.)
Sandi Stretch Shift Dress (This is another gorgeous classic dress that is white lace at the top, and light blue at the bottom.)
Tisbury Shift Dress (I featured this dress in my Easter Dress Shopping Guide, but it’s worth mentioning again here because it’s very similar to a Lilly dress I wore on Kentucky Derby Day five years ago.)
Tessa Dress (Another classic seersucker Lilly dress with lace appliqué detail around the waist. And it has pockets too!)

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:

Vineyard Vines Seersucker Sleeveless Shirt Dress (This has a printed belt that comes with it!)
Vineyard Vines Party Seersucker Shift Dress (Love the color blocked seersucker)
Vineyard Vines V-Neck Fit & Flare Dress (Gorgeous pink dress from Vineyard Vines’ Derby collection.)
Lauren James Eden Wrap Bow Dress (Save 15% with code PINEAPPLE15)
Lauren James Livingston Dress (Comes in pink and blue seersucker and has precious bow detail in the back. You can save 15% with code PINEAPPLE15 on this one as well.)
Draper James Gingham Love Circle Dress (Love this precious gingham number from Reese Witherspoon’s lifestyle brand)
Draper James Embroidered Gingham Dress (Same pattern as the dress above, but has spaghetti straps and embroidery detail at the hem.)

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 six years ago. But here are a few options I found that would be a great complement to your Kentucky Derby party dress this year:

Draper James Straw Hat (Has a gingham band detail!)
Vineyard Vines Kentucky Derby Straw Bow Hat (Very classic and will match any dress.)
J.Crew Factory Textured Summer Straw Hat (A much more budget-friendly option.)
Target “A New Day” Floppy Hat (Has a thin metallic bow detail.)
Old Navy Floppy Straw Hat

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.

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 and hats I mentioned in this post. Click on any picture, and it will take you directly to the retailer’s website:



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