Kentucky Derby Outfit Inspo

The Kentucky Derby is in less than two weeks! I’m not super into horse racing, but I am super into any occasion that involves wearing a cute sundress and floppy hat. I’ve never been to the Kentucky Derby before, but would like to go someday simply because I would love picking out the perfect outfit. In the meantime, I enjoy dressing up to watch from afar. Several years ago I went to a big Derby party. But for the most part, I usually watch with a small group of friends. The sundress + floppy hat combo screams “Kentucky Derby outfit.” So today, I’m sharing some of my favorite sundresses and floppy hats that are currently available. Hopefully this will help y’all select your perfect Kentucky Derby outfit, regardless of where you are watching!

(*Note-this post contains affiliate links. I may earn a commission from clicks or purchases made through these links, at no additional cost to you.)

A Favorite Past Kentucky Derby Outfit

For starters, I want to share this favorite ensemble that I wore on Kentucky Derby day four years ago. My best friend and I went to Top of the Hill, a popular spot in Chapel Hill, to watch the Derby. We were able to sit on the outdoor patio that gives a bird’s eye view of downtown Chapel Hill. Then afterwards we went and took pictures on campus.
Kentucky Derby Outfit

Kentucky Derby Outfit
I wore the Lilly Pulitzer Adeline Dress in pink seersucker. This dress is actually from Lilly’s Spring 2012 line. I seriously think this is one of my favorite Lilly dresses ever. I adore the classic pink seersucker, and the ruffle detail. Honestly, nothing says “Kentucky Derby” like a seersucker dress in pastel colors. My hat is also Lilly Pulitzer, and was a gift with purchase about five years ago. (You may remember this hat from my Easter post.)

My bag is the Tory Burch Amanda Hobo. I have had it for over four years now, so it is no longer available for purchase. But here’s a similar Tory Burch bag that I love. I’m wearing my bronze classic Jack Rogers sandals. Here’s some similar metallic Jacks.

Currently Available

No worries that the Lilly dress above is no longer available, because there are many great seersucker dress options for your Derby Day attire this year. I have shared a handful of them below. You can click on the pictures to go to the retailer’s site and get a closer view and additional details:



A Kentucky Derby party is one of the few occasions I get to break out my special Lilly hat. It’s not currently available for purchase either, but no worries- I’ve got you covered. Here are a few hats that would top off your perfect Kentucky Derby outfit!


Final Thoughts

Another dress I haven’t mentioned yet that would make a perfect Kentucky Derby outfit is the Lauren James Harper Dress. If you’ve been following my blog, then you know I’m a bit obsessed with the Lauren James Harper. I actually own it in four different colors! Although I haven’t worn it to a Kentucky Derby party before, I styled my Powder Blue Harper Dress with my Lilly hat during a shoot with Amelia Cassar Photography back in March.

Kentucky Derby Outfit
For more details about the Lauren James Harper Dress and this outfit, click here.

I hope this post has been helpful in providing some inspiration for what to wear for the Kentucky Derby, regardless of whether you will be at Churchill Downs or at a watch party hundreds of miles away. I haven’t completely decided what dress I am going to wear on Kentucky Derby Day this year, but I will be shopping in my own closet. Don’t worry-I will keep y’all posted!
What are y’all’s plans for watching the Kentucky Derby this year? Have y’all picked out your outfit yet? Let me know in the comments!
-xoxo Liz





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!

Leave a Comment