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Head-turning hats, bold dresses, and chic shoes you'll love for race day—and all season long. small outdoor table
The holiday season may be dubbed "the most wonderful time of year," but for preppy style lovers, it's most certainly the Kentucky Derby. The legendary Louisville-based horse racing event is celebrating its 150th anniversary next month, which means there is some outfit shopping to be done.
The key to looking the part for a day at the track comes down to a few simple components: a killer dress with bold colors and patterns galore, and a head-turning hat and fascinator to top the look off. Equally as important: the shoes. You're going to be on your feet all day, so the last thing you want to wear is uncomfortable heels. Oh, and don't forget about the accessories—sometimes it's the little things that make the statement.
To help perfect your look, we've got you covered with style tips and the best outfit ideas to wear at Churchill Downs, below.
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.
We rounded up some hat ideas to shop this year:
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.
Though classic wide-brimmed hats might be the most common Derby toppers, "understated" is the last thing you're looking for when it comes to a Derby Day chapeau. Consider race day a chance to really go wild with an over-the-top style like this oversized floral option.
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.
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 Barbie pink fascinator with accented feathers? A surefire way to turn heads.
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.
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.
Prefer to keep your outfit more low-key? A hint of draping and a-symmetrical touches will beautifully offset a dramatic topper.
The ruffle details and the zesty hue add just the right amount of interest to this otherwise simple halter dress. It's statement-making yet not too over the top either.
Not only is this dress flattering on all body types, but it's supremely comfortable too.
The straight silhouette makes this style understated and elegant, but it's the oversized bow at the shoulder that brings the look to the next level.
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.
Between the elegant floral details and the bowed accents on the bodice, what you have here is a dress that'll turn heads left and right at Churchill Downs.
Take a page out of Kate Middleton's style book and go for polka dots.
The Derby is no time to blend in—here's your chance to make a statement. Stand out by combining maximum color with maximum length.
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.
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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