Enter here for a chance to win the 'Who Knew?' prize!


Kentucky Derby attire: Outfits and inspirational looks for race day

Everyone knows you’re supposed to wear a sundress and hat to the Kentucky Derby. It’s right up there with drinking mint juleps at noon — and goodness knows we’re not questioning that.

Closed Captioning
apply | reset x

Tara Lipinski shares tips for making the perfect derby fascinator

Play Video - 2:35

Tara Lipinski shares tips for making the perfect derby fascinator

Play Video - 2:35

More video

But what if Lilly Pulitzer-chic isn’t really your thing? Heading off to the races doesn’t have to mean sacrificing your personal style. Whether you’re bound for Churchill Downs, a Derby-themed brunch or just looking for general wardrobe inspiration, these alternate takes on Kentucky Derby attire will be a sure bet.

RELATED: Tara Lipinski's 5-step hack for a fun Kentucky Derby hat!

For the trendsetter …

Take preppy staples like seersucker and gingham to the next level by wearing them in fashion-forward cuts. Think of your pastel romper or cheeky two-piece ensemble as a modern lady’s Gatsby suit. And a playful wide-brim boater hat is the cherry on top!


Selby Cutout Romper, $58, Nasty Gal


Knot-Front Halter Top, $98, High-Waist Belted Cropped Trousers, $148, Neiman Marcus


Wide Brim Boater Hat, $69, Urban Outfitters

For the free spirit ...

Let’s be real: You’re here for the party (and the photo ops). But careful, Toto, we’re not in Indio, California anymore. Coachella-fied details like lace-up panels and fringe are welcome at Churchill Downs … so long as you stick to classic silhouettes and modest hemlines. Then, just swap out your flower crown for a fun fascinator and you'll be good to go.


With Awe Due Respect Dress, $99, ModCloth


Johnny Loves Rosie Fascinator with Hibiscus Flowers, $73, ASOS

For the tomboy …

We’re here for a horse race, aren’t we? So this seems like a fine time to channel a breezy, equestrian-inspired vibe. Go for a chambray shift, or pair high-waisted culottes with a sharp silk blouse. Flat sandals and a fedora are all you need to finish the look.


Chambray Shirtdress, $98, J.Crew


White Culottes, $46, Everlane


Panama Hat, $58, Madewell

RELATED: Johnny Weir and Tara Lipinski don (and talk) Kentucky Derby hats

For the traditionalist …

Go ahead and wear a sundress. But do it with a strappy halter or a nautical stripe pattern to make the look feel modernized. As for the requisite floppy hat, dramatic black is a fun change from the same-old straw version.


Cera Dress, $218, Reformation


Striped Sundress, $48, Topshop


Wide Brim Floppy Straw Hat, $36, ASOS