What to Wear to the Kentucky Derby

The Kentucky Derby is a REALLY amazing opportunity to have a party! I’ve been to so many Kentucky Derby parties throughout the years and they are the best ones ever! There’s no pressure, it’s just pure fun. You get dressed up and just enjoy the night! The one question I always get about a Kentucky Derby party is, “What to wear to the Kentucky Derby?” I get it, it’s a great question! You have to wear your Kentucky Derby best, that’s for sure! So whether you’re heading to a party or the actual Derby, let me help!

What to Wear to the Kentucky Derby

What to Wear to the Kentucky Derby

Let’s start with – what is the Kentucky Derby!? The Kentucky Derby is a horse race that is held annually in Louisville, Kentucky on the first Saturday in May, capping the two-week-long Kentucky Derby Festival. The race is a Grade I stakes race for three-year-old Thoroughbreds at a distance of one and a quarter miles at Churchill Downs. The race is often called “The Run for the Roses” because of the blanket of roses draped over the winner. It is also known in the United States as “The Most Exciting Two Minutes In Sports” or “The Fastest Two Minutes in Sports” in reference to its approximate duration. It is the first leg of the American Triple Crown and is followed by the Preakness Stakes, then the Belmont Stakes. Unlike the Preakness and Belmont Stakes, which took hiatuses in 1891–1893 and 1911–1912, respectively, the Kentucky Derby has been run every consecutive year since 1875. The Derby, Preakness, and Belmont all were run even every year throughout the Great Depression and both World Wars (when the Olympics and nearly all professional sports seasons were canceled).

On the fashion front? What to Wear to the Kentucky Derby is easy because it’s the preppy fashion event of the year. Dressing the part for the Derby is the most fun part of this event! You can really have some big fun and some big fashion sense. You can really turn into someone else for this event! You will look smashing and gorgeous and just over the top extraordinary! I’m excited to show you some of my favorite pieces for What to Wear to the Kentucky Derby! There are also some retailers that are perfect for the Derby!

There are 3 pieces that women need to think about when deciding What to Wear to the Kentucky Derby. One – your dress. It’s needs to be spectacular. Two – your hat. You need something that is over the top fabulous. Three – your shoes. You need shoes that will be standout shoes that work perfect with your look from head to toe! One you’ve covered these 3 bases, you will be perfect! You will feel gorgeous and perfect for the Derby!

Let me start with my favorite of all time, Vineyard Vines! Oh, yes… the Vines! They have an actual Kentucky Derby Collection and they are the Official Style of the Kentucky Derby. So if you’re stuck at the beginning as to What to Wear to the Kentucky Derby, go here first! You will just be over the top amazed!

Seersucker Shift DressWe’re proud to be the Official Style of the Kentucky Derby® for nine years now, and this year we’re celebrating with a limited-edition collection that’s brighter and bolder than ever! Rock the color block. Effortless, this fun swing dress is ready for all those outdoor parties.

Vineyard Vines Seersucker Dress

Off The Shoulder Run For The Roses DressRosey and ruffles! Winner’s circle ready, the off the shoulder and ruffled hem detailing catapult this fashionable dress to the top of our trendsetting list. Pair it with your best derby hat for a fun day in the sun!

What to Wear to the Kentucky Derby

Seersucker Sleeveless Shirt DressWrapped in rose. She’ll be the talk of the derby in this cool seersucker wrap dress – The added roses detailing on the collar and tie around the waist elevate this chic Derby dress a subtle show stopper!

What to Wear to the Kentucky Derby

Lace Dress Crowd favorite! Show up to the biggest event of the year in our chic lace dress. We created a stunning and feminine silhouette that flatters everyone, all you need is a show-stopping hat!What to Wear to the Kentucky Derby

Eyelet Margo Shift DressEyelet what I see! Everyone needs a LWD (little white dress). This gorgeous eyelet fabric elevates our warm weather take on the most flattering margo shirt dress silhouette!

What to wear to the kentucky derby

Let’s head over to the other preppy brand I know and love, Lilly Pultizer! I have some fan faves over there, too! Are you ready for me to dish on what to wear to the Kentucky Derby from there! These clothes are over the top preppy, so these would be fabulous for the Derby, too! You can’t go wrong with any one of these options!

Maya Shift DressThere are so many lovely details on this Maya shift. We are swooning over the carefully positioned ladder lace and feminine ruffle details. The lace mixing continues along the bodice of the dress creating subtle borders and big style!

Maya Shift Dress

Tessa DressThe Tessa has everything you could want in a Spring style dress with its feminine tie-straps, side seam pockets, seersucker, floral lace trim… and did we say seersucker? This is truly a classic dress with all the right updates.

Tessa Dress

Addison One Shoulder DressThe Addison is a one-shoulder, fit and flare dress with a feminine pleated bodice and side-seam pockets. We are loving the pink tropics striping for a new and playful take on traditional seersucker.

Addison One Shoulder Lilly Pultizer

Aviana Maxi DressIt doesn’t get more boho chic than the Aviana Maxi Dress with its flowy tiered body, back smocking detail, and removable sash. Perfect from day to night.

Aviana Maxi Dress Lilly Pulitzer

Let’s talk hats! The bigger, the better! They will certainly help you standout and look fabulous at the Derby! You want to make sure you’re seen and NOT just heard!

Organza and Ruffle Hat for the win, light pink!

Kentucky Derby hat

Organza and Ruffle Hat for the win, beige Ruffle and Organza hat

Fascinators Hat for Women Tea Party Headband Kentucky Derby Wedding Cocktail Flower Mesh Feathers Hair Clip

Fascinator For Women

Fascinators Hat for Women Tea Party Headband Kentucky Derby Wedding Cocktail Flower Mesh Feathers Hair Clip

Fascinator For Women

Womens Straw Cloche Derby Fedora

Large Straw Hat

Let’s talk heels! High and fabulous! Go strappy and go tall! Here are some of my faves for the Derby! I grabbed these 3 from Zappos!

Schutz Cadey-Lee

Nude Strappy Heels

Badgley Mischka Lita

What to Wear to the Kentucky Derby

Same Edelman Strappy Heels

What to Wear to the Kentucky Derby

Whether you’re heading to the Derby in Kentucky or not, you will be dressed for success for the party! I hope these options work for you and that you love them as much as I do! Regardless of your age, I know you can make these work for you!

See more about the Kentucky Derby Collection here, too.

What to Wear to the Kentucky Derby was last modified: April 22nd, 2019 by Audrey McClelland
SHOWHIDE Comments (7)
  1. All of the dresses are awesome but I especially love the lace dress! I’ve never worn a big hat like that in my life…it would be a hoot!

  2. These are really great outfit ideas! I especially love the Lace Dress and the Aviana Maxi Dress. They are so pretty!