Billykirk English Walker Hat

Add a touch of old-world elegance to your winter wardrobe with the Billykirk English Walker Hat ($110). Made from 100% wool, this simple, refined cap features a traditional English country shape, a 1.75-inch brim, a leather outer band, and an antiqued brass buckle. Just pick the accompanying outfit carefully, as this is one hat that can go from cool to colossal failure when paired with the wrong duds.