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The Kentucky Derby Puts the Mad Hatter to Shame

See photos of this season’s most extraordinary hats.

(Photo: MAGGIE MAE DESIGNS®)

“I’m out of my mind—Oh my god, I hardly know my name. It’s crazy, always crazy this time of year. It’s hat Christmas.”

That’s Gena Conti, the owner of Gena Conti Millinery, speaking over the phone five days before the 2016 Kentucky Derby. This week is when the final custom-made hats get shipped straight to ladies’ hotel rooms, and Derby-goers wait to don the elaborate hats and fascinators for all to see.

(Photo: MAGGIE MAE DESIGNS®)

The Kentucky Derby, first held in Louisville in 1875, was first inspired by European horse races. The term “derbies” goes back to the 18th century and typically describes a race for three year-old horses, and the Kentucky Derby has become known in the U.S. as “The Most Exciting Two Minutes in Sports.”

But what sets it apart from every other sporting events is the head decoration—the “chance for every female to express her inner Southern Belle,” as the official website states.

(Photo: MAGGIE MAE DESIGNS®)

“The Kentucky Derby is theater, a grand, glorious stage that is now 142 years young,” says Sally Steinmann, a milliner and the owner of Maggie Mae Designs, a one-woman business in Massachusetts. 

“From the fantastic to the sublime, there are no rules or limits when it comes to choosing your Derby hat,” says the Derby website. Many women who don extraordinary hats, however, prefer to keep the rest of their outfit simple, so as to not distract from the brilliance of their hats. 

(Photo: MAGGIE MAE DESIGNS®)

Derby hats are all about expressing creativity and individuality—through flowers, feathers, and color coordination with the rest of your outfit. We’re not so much talking about large-brimmed hats decorated with World of Warcraft figurines or featuring an intricate diorama of Beyoncé’s Super Bowl Halftime Show. It’s more a matter of choosing flowers or feathers to craft an elegant garden or aviary, possibly ornamented with veiling, bows, and ribbon.

“The idea is that you don’t run into yourself at the Derby,” says Conti. “God forbid your hat look like somebody else’s.” Milliners like Conti and Steinmann craft their hats by hand, one at a time.

(Photo: MAGGIE MAE DESIGNS®)

But you’ve got options. You can have your hat made by a professional milliner, or buy one from a department store, Etsy, or Amazon. Some ambitious hat fans even design and make their own headpieces for horse races, tea parties, garden parties, church and social events. 

Dee’s, a craft and gift store in Louisville, Kentucky, has offered hat-making classes for around 20 years. Though their store sees a huge swell in business at Christmas, Derby is in fact their biggest season, says Kathy Olliges, the store’s owner. The season starts in January, hat-making classes take place in February and March, and everything quickly crescendos to the first Saturday in May; this year, Dee’s designed 2,500 hats.

(Photo: MAGGIE MAE DESIGNS®)

Interestingly, despite the Derby being a historic ground for cultural and racial conflict, politics and opinions don’t make it onto people’s heads. It’s very much about style, not statement. Most women go for a classic look, “one that embodies elegance and innovation achieved through color, design and balance,” says Steinmann.

(Photo: Dee’s of Louisville)

However, she adds, “It is possible that some women have worn Derby hats with a conscious intention of making certain political or culturally significant statements.” Steinmann also thinks it is impossible to separate what one calls “fashion” from one’s sociopolitical identities—rather, they are often intertwined and mutually inform one another in very complex ways.

(Photo: Dee’s of Louisville)

Perhaps its easiest to simply enjoy Derby hats, then, as pieces of art. Perhaps they’ll provide you with inspiration in the case that you ever find yourself in Louisville on the first Saturday of May.

Update, 5/4: An early version of this article stated that the Kentucky Derby takes place on the second Saturday of May. Instead, It is the first Saturday of the month. We regret the error.