The Craziest, Best Hats From the Kentucky Derby

Mint juleps; bourbon, sugar, and mint over crushed ice, cloyingly sweet and cold rivulets of condensation streaming down the side of the glass. Horses with names like Mandarin Hero, Angel of Empire, and Mage (spoiler alert: Mage wins the race). And, of course, hats; hats with feathers, colorful hats, dioramas made into hats. The Kentucky Derby, which was held at Churchill Downs in Louisville, Kentucky on Saturday, is the most anticipated horse racing event of the year, drawing a crowd of over 150,000 people. 

Photo: Michael Hickey via CNBC

During the Kentucky Derby, attendees transform into colorful birds, preening and showing off their own patterns, everyone trying to be the brightest and most noticeable. It is the epitome of camp, a culture of garish costumes that has turned into a contest for who can be the most creative. While the fashion of the whole event tends to be over the top, the Derby is best known for its hats. Here are some of the absolute best hats from this year’s race. 

Monochrome Twins

They simply look like dolls. Stunning.

Photo: Jon Cherry via The New York Times

Float like a Butterfly

This headpiece defies gravity and expectations. It is absolutely stunning, and maybe my favorite “hat” from the event

Photo: Brynn Anderson via The Press Democrat

Horse Helmet

They’re horses… that spin… like they are racing. Awesome.

Photo: Brynn Anderson via The Press Democrat

Mother Daughter Look

They look like they are at a wedding, in the best possible way. This is perfect, and adorable, and about twenty other adjectives. 

Photo: Julio Cortez via The Press Democrat

Blue Serpentine Headpiece

Is that a snake or a roller coaster on her head? Either way, I love it, especially paired with that bright orange dress. 

Photo: Jon Cherry via The New York Times

Racetrack Diorama

It’s the Kentucky Derby… at the Kentucky Derby. Genius.

Photo: Jon Cherry via The New York Times

Boater Hat

It’s simply a classic. And with the red blazer and bow tie? Chef’s kiss. 

Photo: Jon Cherry via The New York Times

Gold Halo

I actually have no criticisms here. This is absolutely stunning. She does look like an angel. 

Photo: Jon Cherry via The New York Times

Pink Feathers

Another classic, keeping simple and monochrome with a feather embellishment. Is it just me, or do they kind of look like pink tentacles? 

Classy Green

Simplicity is often best. This looks great. 

Photo: Brynn Anderson via The Press Democrat

Red and Pink Floral

Normally I would hate flowers on a hat, but I have a soft spot for lilies. I bet she smelled great all day. 

Photo: Brynn Anderson via The Press Democrat

Wide Brimmed Pastels

I love the color combination here, and I love the large circumference even more. Go big or go home, right?

Photo: Charlie Riedel via The Press Democrat

Romantic Roses

This looks almost sensual. I think it is very cool.

Photo: Charlie Riedel via The Press Democrat

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