5 Kentucky Derby Outfit Inspirations for the Ultimate Fashionista

The Kentucky Derby is just around the corner and whether you’re hitting a backyard barbecue or walking the historic grounds of Churchill Downs, the event is the ultimate opportunity to show off your outfit. Big hats, pastel dresses and bold designs are key components to Derby dressing.

Yes, it’s about the horse race, but the occasion wouldn’t be so famous without the fashion.

Expressing your personality is essential when it comes to your ensemble so if you’re into a hat that can’t fit through a door, be my guest. It’s part of the Southern tradition, after all. And while hats are truly part of the spectacle (wearing a hat is said to be good luck), your shoes are just as important.

Here are five outfit ideas for the style maven who wants to stick to the Derby theme, but in a more fashion forward and less traditional way.


1. Floral Foundation

Keep your outfit light and fresh with a floral look. This cotton-poplin patterned dress from Veronica Beard offers a sweetheart neckline and flattering ruching. Make the petals stand out with a pair of matching shoes.

If you’re at the track, these Mansur Gavriel block-heeled mules are more than appropriate — not to mention comfortable.

Top off the look with a matching white hat. This Panama-style straw topper is understated, but with the widebrim it still stays on theme.

2. Pretty in Pink

Keep traces of tradition with this pink pastel statement hat. Elegance is added to the Eugenia Kim piece from its two-tone satin-faille ribbon. Let the hat speak for itself, while pairing it with pale pink stilettos and a cream denim pinafore dress.

3. Vintage Provisions

The feminine straw hat embellished with a polka-dot burlap bow takes us back in time. And paired with the broderie anglaise cotton dress from Alice McCall, this look gives a vintage feel — ideal for a racetrack environment. (The Kentucky Derby has taken place every year since 1875.)

Opt for a block-heeled ankle-strap sandal if you plan to be on your feet all day.

4. The Pretty Woman

It’s not exactly a polo match, but there are horses so any excuse to channel Julia Roberts’ “Pretty Woman” character is a must. This satin polka-dot Rancil two-piece ensemble is an update from the outfit seen on Vivian in the 1990 film. And wearing these white structural mules, will have everyone asking where you snagged your shoes.

5. Black Sheep

If you’re one of those people who solely wears black, don’t let the traditional Kentucky Derby colorful customs sway you to choose otherwise. You can still look the part.

Here, the shoes take centerstage, featuring Alexandre Vauthier’s satin polka-dot mules. In addition, Eugenia Kim’s wide-brim mesh hat is simply a game-changer.

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