How to Choose the Perfect Hat for Your Kentucky Derby Party

Lauren Conrad
Lauren Conrad Mike Coppola/Getty Images

Grab your best hat and a mint julep — we're off to the races! The Kentucky Derby 2016 will take place on Saturday, May 7, and more than a few fabulous hats in the crowd will be crafted by celeb milliner Kenzie Kapp.

The hatmaker to stars and stateswomen alike (including Dr. Jill Biden and Miss Kentucky) starts working on her clients' caps long in advance — sometimes a full year! "Some of my most loyal Derby clients start tossing out ideas for the next year's Derby while at the Derby," the Louisville-based Kapp tells Us Weekly. "It's also not unusual for me to get calls from a client in the summer. We go round and round, and by December, we have the framework for the headpiece [in place]."

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Caroline Ford and Katie George
Caroline Ford (left) and Katie George wearing Kenzie Kapp's hats at the 2015 Kentucky Derby. Neilson Barnard/Getty Images

1. Find the Dress Before the Hat

Kapp takes everything into account when creating a client's chapeau, including the shape of her face, her skin tone and her hair color. But none of that matters without a solid foundation. "The hat should be able to stand alone," she notes. That said, "I always suggest finding a dress first, because most women are more familiar and comfortable with shopping for a dress."

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Jackie Kennedy and Kate Middleton
Two iconic hat lovers, Jackie Kennedy (left) and Kate Middleton. Bettmann Archive via Getty Images; Indigo/Getty Images

2. Get Inspired by the Classics

Headpiece or fascinator? That's the endless question, which even Duchess Kate surely grapples with. When trying to choose the right hat for you, look to some of your favorite moments of all time. Jackie Kennedy's pillbox hats, the embellished cloche hat of the '60s and even Will Smith's flat cap in The Legend of Bagger Vance all make Kapp's shortlist.

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3. Don't Be Afraid to Go Bold!

Kapp has one last tip for you Derby ladies, and that's to go big or go home! "You can’t celebrate Derby without dressing up! And [in this case], the words 'too much' don’t exist," she says. "The Derby is all about looking good, feeling great and having fun. A great outfit, cool headpiece and cold drink will always work, regardless of the party's location, stylization or sophistication."

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