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.