You don’t have to be a betting man or lady to bank on this: you’ll see more memorable outfits on Derby Day than memorable races. The 1.25-mile horse race only lasts for two minutes, but what you wear to it can last a lifetime (depending on how many pics you take). Ladies and gents go all-out in the fashion department on Derby Day, donning lavishly decorated big-brim hats, elaborately patterned sports jackets and dresses designed for Southern Belles

Anyone who revels in good, old-fashioned creative styling will love this springtime style event. After all, it’s all about standing out with the big, bold and bespoke, from funky-patterned bow-ties to hand-adorned hats. Whether you’re heading to Churchill Downs for the big race or just plan on celebrating at a derby-themed party on the first Saturday in May, the following looks will surely inspire proper derby dressing.

All About the Hat

Wide-brimmed straw fashion hats have been a Kentucky Derby mainstay since 1875 when founder Col. Meriwether Lewis Clark Jr. launched a campaign to make the derby a place for the upper echelon of society rather than one for gambling, drinking and vices. His campaign worked, and that year’s grandstand was filled with hundreds of spectacular hats handmade by Louisville milliners. The popular thing to do at the time was for women to coordinate their outfits for the derby—hats, dresses, shoes, bags and parasols—as if they were heading to a ball or a cocktail party rather than a sporting event.

At the time of Clark’s brilliant marketing ploy, hats were ubiquitous, especially among the upper class. Now, fancy and elaborate straw hats are less common, worn almost exclusively on special occasions—to church on Easter Sunday and to the derby once a year. And you can’t go to Churchill Downs without a hat. After all, the derby hat is as talked about on Derby Day as the predicted front-runners. Any good derby ensemble begins—and, arguably, ends—with a chic wide-brimmed hat. Complete your look with a few more Southern wardrobe staples and you’ll be well on your way to a winning style.

Ladies: No, the Hat Isn’t Optional

If you’re thinking about showing up to the grandstand sans a topper, think again. While the staff at Churchill Downs most likely won’t kick you out if you aren’t wearing one (though they do have a few dress codes to follow, depending on where you watch the race), you’ll definitely feel out of place if you go “naked” on the head. A good rule of thumb is to start your derby outfit with a hat and work downwards. Here are the fundamentals of a good derby outfit for women:

  • The Hat—Derby hats may be large like classic derby-style wide brims or small like chic fascinators, handmade or homemade, but they all have one thing in common—they’re distinct from everyone else’s. Your derby hat may be classically embellished with feathers, flowers, grosgrain ribbons and elaborate bows or made into something novel and borderline wacky. To make it all your own, you might even select a monogrammed derby hat to get in the spirit. As long as it stands out and isn’t easily replicated, you’ve got the right idea.
  • The Dress—Though less important than the hat, the dress is a core component of a good derby ensemble. Ladies tend to gravitate towards pastels—it is May, after all—and stick to classic Southern silhouettes, especially the tea- and calf-length. Spring dresses done in fun, flowery patterns and bright colors are always a hit on Derby Day.
  • The Accessories—No special occasion outfit is quite complete without some chic accessories, but remember that on Derby Day, your outfit should let the main attraction—that is, of course, the hat—take center stage. Accessorize with delicate jewelry so you don’t distract from your topper. Traditionally, ladies sport strappy sandals and heels but keep in mind that you may do a lot of standing while spectating, so comfort is key.

Gents: Derby-Worthy Suits

Guys, don’t feel left out! While your hat won’t be quite as talked-about as the ladies’, it’s still a welcome and encouraged addition. Men can join the fun by adding a straw bowler, fedora or pork pie hat to their ensemble, especially one that has been handmade or altered just for the derby. Whether you hot-glue plastic horses over the brim or keep it classic with a grosgrain ribbon over Panama straw, you’ll feel right at home when you’re sporting your derby hat in the grandstand or at your big derby party.

Perhaps more important than the hat, for the men, is the suit. Guys are encouraged to wear all sorts of bold and whacky spring suits, from pastel-colored linen styles to those done collar to cuff in funky tropical prints. If you want to adhere to a more classic suiting style, stick to seersucker, linen or chambray done in a subtle color or pattern. Guys at the derby also often rock bow-ties, especially ones done in statement patterns. Basically, the bolder the suiting the better when it comes to men’s derby fashion! Get as creative as you’d like.

An Iconic Southern Event

If you’re throwing your own derby watch party, make sure to include the dress code on the invitation so that everyone knows what to wear. Don’t forget the wording “Creative hats required” and get excited to see what your guests come up with! So long as you’ve got a hat on your head and a mint julep in hand, you’ll look like a seasoned derby pro, even if it’s your very first rodeo.


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