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Kentucky Derby Designer Hats For Women

Kentucky Derby Designer Hats For Women

Springtime heralds the arrival of the renowned Derby Week at Churchill Downs in Louisville, Kentucky. The celebrated Kentucky Derby is scheduled for May 4th, 2024, coinciding with the 150th anniversary of the legendary Churchill Downs racetrack. A gathering of millions dress in their finest, creating a vibrant fashion spectacle for America's most prestigious horse race.

Kentucky Derby Designer Hats for women.

Kentucky Derby Attire for Women

Wondering what to wear to the Kentucky Derby? The event calls for a unique blend of "Southern charm and urban edge" in its dress code. It's recommended for racegoers to double-check the Churchill Downs website, as certain sections and clubhouses may have more specific dress code requirements.

With a wide array of creative hats and fascinators to choose from, finding inspirational headwear allows you to build the rest of your outfit.

Kentucky Derby Women's Hats

Vivien Sheriff Fun of the Fair latest headwear collection is designed to thrill and spark joy with its vibrant colourways, sculpted dazzling detailing and head-turning sweeping brims. So, if you’re looking for style inspiration for Kentucky Derby day dressing, here are 7 recommended headwear picks to empower the Southern Belle stylist in you!

Kentucky derby women's hat

Toffee Apple

This magnificent statement hat with elevated brim in sweeping sinamay serve to elongate the body shape for an elegant statuesque look. Not only does it add extra height, but its also skilfully festooned with soft fabric orchids in gentle tones adding 360 degrees of captivating interest. For an extra refined look, try styling these show-stopping beauties with a mid-length dress coat and an elegant pump / court shoe.

For impact, choose your dress, shoes and bag all in the same single colour, one that blends with the hat’s floral detail. 

Wide Brim Kentucky Derby Hat

Exquisitely romantic and reminiscent of a bygone era……think pony and traps, parasols, lace gloves and handkerchiefs; these vintage inspired head-turners would cause many a heart to swoon.

women's hats at the Kentucky derby

The Juggler

wide brim kentucky derby hat

Victory Gallopers

Designer Kentucky Derby Hats

Sweeping sinamay disc hats don’t tend to get more splendorous than these two showstoppers. These bold styles are sure to catch the attention of other racegoers for all the right reasons. Black and white attire is a classic style combination. Whether you choose a bodycon striped dress, a polka dot frock, or a pure white or black jumpsuit to match Helter Skelter, the effect will be ultra-stylish, no matter your choice.

designer Kentucky derby hats

Helter Skelter

When choosing coordinating outfits, opt for the bright colour tones found in the Big Dipper splash of feathers for a maximalist look.

best Kentucky derby hats

Big Dipper

Kentucky Derby Fashion Hats

Like a bold statement, then perhaps one of this sinamay mid-disc in bright pink is the perfect hat for you. Expertly hand-crafted and well-balanced to complement various shapes and heights, this charming disc hat effortlessly pairs with a variety of dresses.

Kentucky derby fashion hats

Roller Coaster

Kentucky Derby Straw Hats

If practical glamour is your style identity, then look no further, than this glorious straw hat. Not to be underestimated, this whimsical straw hat possess the power to turn-heads by the artistry in its form and structure.

kentucky straw hat

Coconut Shy

Not only is it  beautiful, but also functional providing ample shade to keep you looking cool, calm and composed all day long. See the full collection of designer straw hats 

A few final tips……

Springtime weather in Louisville is never guaranteed, so it's wise to pack a lightweight, packable waterproof cape. Finally, remember, it's reportedly good luck to wear a hat to the Kentucky Derby. No festival outfit truly achieves its full potential without the crowning touch of a stylish Vivien Sheriff hat!

For further styling inspiration, browse the selection of hats and fascinators here or look through the Spring summer section at For one to one styling advice and a hat fitting, you can visit us at our UK based Wiltshire showroom or schedule a virtual appointment with a team expert by emailing or calling ++44 (0)1725 512983.

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