11 Winter Hats That Won’t Make You Look Dopey

Canvas Trapper Hat With Rabbit Fur($35)

Once a style reserved for flyboys, the kid who gets his tongue stuck on the pole in A Christmas Story, and Snoopy, this retro look has undergone a revival in recent years. It’s tougher to pull off than a traditional stocking cap, but if you can, we’re pretty sure you’ll automatically be allowed to fly prop biplanes.