13 Kentucky Derby Hats You Should Probably Never Wear To The Race

What could possibly add more allure to a Kentucky Derby ensemble than a jaunty hat? If you choose the wrong topper, the answer is just about everything. Kentucky Derby hats have a long and quite literally colorful history of innovation, from horse chapeaus to straw fedoras and every possible iteration in between, many of them gravity-defying and bizarre. Why Derby attendees choose to glue stuffed animals and dioramas to their heads remains a mystery, but what is clear is how incredibly daft these hat-wearers appear in their creations. If you plan on attending the Derby with a statement topper in tow, read on for 13 hats that should absolutely be forbidden from the occasion.

The Hypnotic Hat

For the sake of other derby attendees, refrain from wearing a hat that could cause vertigo.

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The Nouveau-Shamrock Hat

A chapeau that bears a striking resemblance to a shamrock, mossy log, or any other natural element you might find in the thick of a forest doesn’t belong at the Derby.

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The Horse Hat

The only horses at the Kentucky Derby should be those racing on the track — not attendees who find the notion of donning animal likenesses amusing.

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The Figurine-Adorned Floral Hat

Derby toppers are trippy enough without the addition of miniature figurines that appear to be climbing through a forest of blossoming roses.

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The Beanie Baby-Accented Hat

Hand-decorated hats may be a hallmark of the Derby, but superglued Beanie Babies cross the line into the territory of Rachel Berry’s Glee Lady Gaga costume.


The Feathered, Ziegfield Girl Hat

Any hat that might have been worn by a Ziegfield girl in the early 20th century should be eschewed by attendees of the Derby.

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The Horse Diorama Hat

A hard hat with horses on propellers is more akin to a modernist art project than a hat.


The Architectural Model Hat

However impressive they may be, architectural models seem like an incredibly painful and weighty substitute for a perfectly passable straw fedora.


The Swirling Vortex Hat

Your head should under no circumstances appear to disappear into a swirling vortex. If your hat creates such an illusion, abandon it immediately.

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The Clown Hat

Unless you intend to perform a comedy routine, save the clown chapeau for a child’s birthday party.

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The Overly Ornamental Tricorn Hat

If it appears as if you could easily buckle under the weight of your hat, the chapeau probably shouldn’t be worn in the first place.

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The Vision-Obstructing Hat

A hat should under no circumstances obstruct your vision, especially when galloping horses are mere paces away.

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The Five Story Hat

If you’re five feet tall without your chapeau and gracing treetops with the topper, the hat is simply too colossal.

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