Flair Affair: Best Kentucky Derby Hats

It's the biggest horse race in the world, but let's face it — the Kentucky Derby isn't just about the thoroughbreds galloping around the track. This grand sporting event has also become one of the biggest fashion shows of the year.

Every spring, on the first Saturday of May, Derby goers descend upon Churchill Downs in Louisville, Kentucky to flaunt their outrageous best.

From over-the-top fascinator hats to swishy top hats, cool cowboy hats to sun hats festooned with frilly florals, the spectacle of festive hats is not to be missed. And it’s not just women getting in on the eye-catching action — mens Kentucky Derby hats are no less a sight to behold.

Whether you're heading to Louisville or simply celebrating with a Derby party of your own, we've got you covered with the best hats to complete your Kentucky Derby outfit. But first, we're helping you brush up on your Derby trivia and etiquette.

Run for the Roses

Flair Affair: Best Kentucky Derby Hats

The Kentucky Derby has been held every year in Louisville, Kentucky since 1875. While it has a few nicknames, including "The Most Exciting Two Minutes In Sports," it's most often called "The Run for the Roses," which refers to the blanket of roses draped over the Kentucky Derby winner each year.

The race itself is the culmination of the two-week Kentucky Derby Festival, which first ran in 1935, and features the Great Balloon Race, the Great Steamboat Race, the Pegasus Parade, and Thunder Over Louisville, the festival's kickoff event that holds the title as the largest annual fireworks show in North America.

Derby Do's and Don’ts

Best Kentucky Derby Hats

Fashion has always been an important part of the Kentucky Derby, but it wasn't until the 1960s that flamboyant headwear became the primary spectator sport. While the Kentucky Derby doesn't have the regal pomp and circumstance of a royal wedding, it comes pretty close — with a sprightly Southern twist, of course. Here are a few things to keep in mind when attending the main event or hosting your own viewing party.

Derby Hat Winners

You're an original and your hat should be, too. Shop some of the best Kentucky Derby hats for a red-carpet look that will take you to the races in style.

York Beach by Brooklyn

Flair Affair: Best Kentucky Derby Hats - York Beach

If you prefer to turn heads with more class and less flash, look no further than this two-tone straw hat carefully crafted from handwoven Ecuadorian straw. Designed with a 4-inch wide brim, domed crown, and sophisticated grosgrain band, York Beach hat by Brooklyn plays it cool so you can let the rest of your outfit shine.

Paddock by Scala

Flair Affair: Best Kentucky Derby Hats - Paddock

You can't go wrong with a classic boater hat and the Paddock straw hat from Scala hits the spot. Hand-woven Ecuadorian Panama straw is accented with a striped grosgrain band and 2 3/8-inch brim for a look that is dexterously dashing. Pair this piece with a gingham button-down shirt and tailored jacket or a colorful bow tie and suit for a winning combo on Derby Day.

Lipizzan by Scala

Flair Affair: Best Kentucky Derby Hats - Lipizzan

Put this hat on and get ready to channel your inner Southern belle. Boasting an over-the-top 8-inch brim topped with a whimsical bow and matching feathers, Lipizzan by Scala embodies the gossamer glamour of Derby Day. Try it in lilac for a feminine flourish of "flower power" or turquoise for a look that floats on your head like an alluring sea.

Legacy by Biltmore

Flair Affair: Best Kentucky Derby Hats - Legacy

When you want a hat that's pure money, the Legacy fur felt fedora by Biltmore fits the bill. From the suede finish fur felt to the grosgrain band punctuated with a flared feather, this short-brimmed fedora is quality through and through. And let’s not forget the satin lining and stylish windcord, which will keep this topper in place no matter what the day brings.

Falabella by Scala   

Flair Affair: Best Kentucky Derby Hats - Falabella

Roses are the official flower of Derby Day, so why not pick a hat in an eye-catching crimson hue that would go perfectly with a floral dress? Composed of gauzy sinamay fiber, Falabella by Scala exudes Southern charm with an organza flower and feathers that sit above a 4-inch layered brim.

Cotton Candy by Scala

Flair Affair: Best Kentucky Derby Hats - Cotton Candy

You’re the kind of guy who makes a splash wherever he goes, so why would the Derby be any different? The Cotton Candy top hat by Scala is an ingenious twist on an old classic that’ll make you feel as though you have your own wearable piece of street art.

Riders Up!

Find the Best Kentucky Derby Hats

There's no doubt that the Kentucky Derby is one of those time-honored traditions that has captured the imagination of people not only in the United States, but around the world. Over the years, it's grown beyond horse racing into something of a hat lover’s paradise for both men and women. And why not? Maybe the race track isn't so different from a fashion runway.

After all, if you think about it, the horses aren't the only ones dashing across Churchill Downs to reach the finish line — women and men prance around the grounds hoping to best each other's over-the-top fashion. Whether you're heading down south or just want to play dress up for a day, check out our full selection of Kentucky Derby hats for women and men.

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