Shop Draper James

What to Wear: Kentucky Derby Fashion

150th anniversary of the Kentucky Derby logo.

What is the Kentucky Derby, Anyway?

This year marks the 150th running of the Kentucky Derby, the greatest two minutes in sports! Each year, the 20 top ranked three-year-old Thoroughbred race horses and their jockeys show superior athleticism and grit in Louisville, Kentucky—the neighboring town to our Lexington store (located at the Summit at Fritz Farm). But the event isn’t only known for the talented horses or historic garland of roses presented in the winners circle: the Kentucky Derby fashion (and a delicious mint julep) are what we’re here for!

Kentucky Derby Fashion

In Louisville and surrounding areas of Kentucky, derby celebrations last the entire week leading up to the Grade 1 Stakes race, which offers locals and visitors plenty of time to show off their best Derby outfits. At Draper James, we never miss a chance to dress up and show off our fun, feminine, confidence-inspiring style, and neither should you. Whether you’re attending the Derby in Louisville or heading to a derby party closer to home, the key to Kentucky Derby fashion is simple…have fun with it! Dressing in fun colors, prints, and patterns, with a matching handbag and shoes, and of course dawning an ever-popular derby hat are all part of the show.

Kentucky Derby Dresses

When talking Derby dress fashion, more is more—bright colors, bold florals, ruffles, you name it. You’ll want a dress with at least one, or all, of these attributes. Those attending the race at Churchill Downs should always consider outdoor conditions and weather in their fashion choices (especially if watching from the in field or in a Turf Club box…you’ll thank us later).

Draper James dresses are designed in many variations and styles, so you’ll be sure to pass the attire requirements of your local Derby party or seating area at Churchill Downs (the higher up you are in the clubhouse, the fancier the attire). As with most occasions, we could go on and on about our favorite event dresses. But in the interest of time, our recommendation for Kentucky Derby event dresses begins with the Carrie Smocked Dress in poppy-printed linen. It stands out in a crowd and makes for a fantastic outfit in photos. As one of Draper James’ best-selling silhouettes, it’s a show-stopping dress that will for sure earn a few compliments at your derby party or on Derby Day. It’s one of Reese’s favorites, too!

Some other popular picks are the Wilson Mini Dress and the Zoe Circle Dress. The Wilson Mini is a cheeky, above-the-knee length pink dress perfect for warm sunny weather or any indoor event. Our Zoe Love Circle Dress is made of cotton so it’s cool and breathable, with the right amount of structure and stretch to make your Kentucky Derby fashion choice comfortable and fun. Its simple, yet flattering striped pattern can be dressed up to fit any seating area of Churchill Downs or backyard party. This dress pairs well with almost all types of accessories, and you can’t forget the shoes! Dress it up with a heel for path walking, or dress it comfortable with a wedge heel or flats.

Another favorite is the Katie Midi Dress. It’s cut from a bold dot jacquard fabric and features a bright poppy print. Bracelet-length sleeves offer spring style for a cool weather day and still leaves room for lots of Draper James accessories. Complete the look with a gold charm bracelet, complete with horseshoe charm!

For warmer wear, the Poplin Lindsay Shift dress is a fab option. It offers the perfect amount of stretch and long sleeves for a cooler spring breeze. And, for the ladies that may get a little cold at an air conditioned indoor derby party, our Mariner Quarter-Zip Sweater draped around your shoulders is a great solution to stay warm while keeping in Kentucky Derby fashion. 

A Kentucky Derby Staple: Derby Hats and Fascinators

If you’re even somewhat interested in fashion you’ve likely heard the hype around hats at the Kentucky Derby. While some may disagree, Churchill Down traditionalists say hats are the most important part of any derby outfit for male and female spectators. According to Kentucky Derby history, hats are considered good luck—for the horses and for those placing bets on them. As the story goes, the bigger the hat, the better the luck. Traditional Kentucky Derby hats were bold, brightly colored, and had brims that offered shade for two (at the very least). Today, Derby attendees wear them because they’re a fun fashion piece to add to any style look. As an added bonus, they can make it easier for friends to spot you in a crowd. 

If you’re seated outside for the race or attending an outdoor party and looking for a little sun protection, our Straw Fedora and larger-brimmed Chambray Herringbone Hat are both excellent choices. You can even personalize and dress them up with some custom flair—feathers, ribbons, tulle, stuffed birds, or whatever tickles your Derby Day fancy.

In recent years, many female Derby-goers have opted for fascinators over the long standing hat tradition, in large because they can be easier to pair with your hairstyle and more comfortable for all-day wear. We’ve even created our own Draper James Fascinator in fun and flirty navy! Fascinators are also an appropriate Kentucky Derby fashion choice no matter where you’re seated at Churchill Downs—from the in field to Millionaires Row.

Accessories for the Kentucky Derby

Traditional derby day accessories are also…you guessed it…bold. When choosing footwear, you want to be comfortable and safe walking around Churchill Downs. Unless you’re celebrating from afar, think of your footwear for derby day the same way you might for a day at Disney. Skip the super-high and spiked heels, or anything you can’t walk or stand around in all day.

Wedges, like our Olivia Wedge, are a perfect solution for the grandstands and the in field. They’re cute, comfy, with a little bit of height to boost your view of the track. Our Paloma Platforms, meanwhile, are secretly comfortable, with a walkable stacked heel and memory foam padding. If you’re watching in person, some Derby vets swear by a pair of flip-flops tucked into their bag (though be sure to check the rules on bag sizing before you go).

Other accessories to complete your race day look, like jewelry or a cute bag, can be found at Draper James, too. Whether your style is silver, gold, pearls, or bright colored bedazzled stones, our selection of earrings, necklaces, and bracelets has something for every style. As mentioned, those attending race day in person will want to review Churchill Downs bag size requirements before selecting the perfect purse. The Frame Textured Clutch or Micro Hobo in Light Blue should both pass the bag check with flying colors for both size and style! 

Make Memories at the 150th Kentucky Derby

Regardless of the fun style choices you make, or whether you’re able to attend an in person viewing or laid back far away event, the best part of attending any derby celebration is watching the final race! With all the flirty and elegant derby day fashions, it’s easy to be distracted from the intended main event. So we’ll remind you once more to cheer on your favorite horse and rider during this year’s 150th running of the Kentucky Derby. We’re sure you’ll look great doing it!

Welcome to the Draper James blog. My little slice of space to share the things I love most about life: people, parties, food and fun! It’s everything Draper James stands for and I hope you like it. 

Follow Us



You May Also Like

Welcome to the Draper James blog. My little slice of space to share the things I love most about life: people, parties, food and fun! It’s everything Draper James stands for and I hope you like it.