Culturally Relevant Hats to Consider for Your Kentucky Derby Party

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Happy Kentucky Derby weekend! The Kentucky Derby is an event famous for its traditionally elaborate hats, which, in some circles, range from the demure and graceful to the wild and bombastic, depending on the disposition of the lady (or gent!) nestled underneath. Needless to say, the hat you choose for today’s derby festivities says a lot about you, and perhaps even more about your goals for this year’s party. If you’re at a loss as to what kind of hat might be most appropriate for your personality and/or Derby social goals, we’ve selected some stellar options from culture and history for you to choose from. Click through for some sartorial inspiration, and let us know your own hat picks in the comments.

Napoleon’s bicorne chapeau

To Wear If: You want to show everyone who’s boss — and maybe add about a foot to your stature. Not that you need it!

Aretha Franklin’s inauguration bonnet

To Wear If: You plan to outshine the host, and the guest of honor.

Audrey Hepburn’s wide brimmed Breakfast at Tiffany’s vision

To Wear If: You’re looking for a husband with millions of fine qualities.

Jack Sparrow’s tricorn extravaganza

To Wear If: You’re only even at this party for the free liquor.

Indiana Jones’ adventure cap

To Wear If: You’re vaguely worried that the party is being held on top of an ancient Indian burial ground. Or that the hosts are communists.

James Dean’s giant cowboy hat

To Wear If: You’re so handsome you can literally pull off anything.

Jackie O’s pillbox hat

To Wear If: All the boys already know who the real star is.

Really any of Lady Gaga’s hats, particularly her hair hats

To Wear If: You’re marking your territory as the empress of this party/season/year/universe.

Charlie Chaplin’s bowler

To Wear If: You’re the quiet type, but still the life of the party.

Mad Hatter’s bizarre top hat

To Wear If: You brought the drugs.