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Here's What to Wear to the Kentucky Derby
Head-turning hats, bold dresses, and chic shoes you'll love for race day—and all season long.
While sports fans might insist that racing is the real point of the Kentucky Derby, fashion fans know the truth: it's all about the looks. After all, how many opportunities do you get to don a truly over-the-top hat or indulge in your most preppy-perfect patterns and prints?
Since it would be a shame to waste this sartorial opportunity—whether you're heading to Churchill Downs or throwing a race day party at home—now is the time to start getting your outfit together. To get the complete vibe, you're going to need: A) a head-turning hat (yes, even non-hat lovers can be converted for one day a year) B) a great dress that's stylish, comfortable, and makes the most of the day's edict to stand out, and C) complementary accessories including a pair of shoes that you cant stand up in all day (trust us, you'll thank us later.)
To help perfect your look, we've got you covered with style tips and the best outfit ideas to wear at Churchill Downs, below.
Start With Your Kentucky Derby Hat
No Derby outfit is complete without a hat. While wide-brimmed hats are the most popular style, there's really no limit to how creative your headwear can get. In fact, wearing a hat to the Derby is reportedly good luck, according to the Derby itself. A word of warning, though: the rest of your outfit will likely revolve around your hat, so choose wisely.
There's a time and place to dress minimally, and the Kentucky Derby isn't it. Go big and bold with a bright red hat accented with an oversized bow to seal the deal.
While straw hats are often reserved for the gents on Derby day, who says the ladies can't don one? An eye-catching ribbon is an elegant way to dress up a more understated straw topper, and this one is giving us serious Eliza Doolittle vibes.
For a more modern and minimalist hat that still makes an impact, a shallow boater style brings a sophisticated feminine touch.
Try a Fascinator
Fascinators—smaller headpieces worn on a headband or a comb—have also become popular at the Derby in recent years, thanks to fans of the British royal family. Many royals, including Kate Middleton and Meghan Markle, have been photographed wearing elegant fascinators through the years, sparking a surge in interest.
Here are a few fascinators to shop for this year's Derby:
A petite topper with a veil is a great opportunity to go all-out on color and detail. Better still: It'll go with any dress style, whether it's solid or whimsically-printed.
"Understated" is not a watchword for Derby style, so embrace the maximalism with plenty of embellishment, florals, and height.
A smaller size doesn't have to mean low drama—take the opportunity to go for some eye-catching height like with this white and black disc fascinator.
Opt for Solids for Your Derby Dress
There are two schools of thought regarding Kentucky Derby dresses: some attendees want to let their hats shine, so they choose a simple dress with an understated silhouette and limited embellishment. Others want their dresses to be the main event, so they'll choose a subtle hat to pair with a brightly colored or patterned dress instead.
If you're solidly in the solids camp...
A solid-colored fit and flare dress adds some playful flounce and keeps you comfy all through race day. You can't go wrong with this Dress the Population number: it's vibrant, flattering, and even comes with handy pockets for holding your essentials. And with nearly 2-dozen shades available, it's a sure match for watcher you decide to wear.
Prefer to keep your outfit more low-key? A hint of draping and asymmetrical touches will beautifully offset a dramatic topper.
Lace is always a popular choice for the Derby, and this ladylike version, from royal-loved brand Self-Portrait, even comes with its own built in necklace, so you have one less accessory to decide on.
A super juicy shade, like this neon green, lets the dress do all the talking, despite a relatively simple shape.
Or Rock a Bold Patterned Dress
Since the Kentucky Derby is all about channeling your inner Southern Belle, it's essential to incorporate bright colors, fun florals, or a classic print. A bold style is particularly great for a guest who wants their dress to be the conversation starter.
What better for the Run for the Roses than a rose-patterned dress, made extra femme by a bow-bedecked bodice?
The mix of gingham and bows is preppy perfection—and ideal for the Derby.
The Derby is no time to blend in—here's your chance to make a statement. Stand out with an eye-catching pattern like this black and white botanical motif.
The blue and white color combo brings the classic touch, while this asymmetrical floral print keeps things modern and fun.
The Derby Day Shoe Game
Chic summer sandals, open-toed heels, or chunky pair of espadrilles will do the trick on Derby Day. While the actual Derby race only lasts a few minutes, the day as a whole is quite lengthy, so make sure you're wearing a comfortable pair of shoes.
A pair of espadrille wedges are not only comfortable and sturdy but are ideal for anyone at the race track on Derby day. Consider these Kate Spade sandals featuring a slim ankle strap and girly bow detail.
Lauren Hubbard is a freelance writer and Town & Country contributor who covers beauty, shopping, entertainment, travel, home decor, wine, and cocktails.
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