No question, a guy in the right hat is, well, a beautiful thing. While most men find it harrowing (to say the least) to identify the right accessories to punctuate their style, a good-looking hat can do wonders for finding discovering a dude's inner gentleman. And with the cool winds blowing, there's no better time to dabble in some down-and-dirty lid sampling. 
Clockwise, from left: Urban Outfitters Wool Beanie, $28, available at Urban Outfitters; Rag & Bone Porkpie Hats, $150 each, available at Rag & Bone NYC; Victor Osborne Roland Hat, $275, available at Revolve Clothing.
From left: Patagonia Wooly Hat, $35, available at Patagonia; Urban Outfitters Mad Wax Bomber Hat, $32, available at Urban Outfitters.
Clockwise, from left: Patagonia Visor Beanie, $35, available at Patagonia; Obesity and Speed Thermal Hat, $44, available at Oak NYC; Filippa K Melange Hat, $89, available at Achilles.
From left: Urban Outfitters Russian Bomber hat, $32, available at Urban Outfitters; L.L. Bean Mad Bomber Hat, $39.50, available at L.L. Bean.
Clockwise, from left: Opening Ceremony Lumberjack Cap, $143, available at Tobi; L.L. Bean Warden's Hat, $45, available at L.L. Bean; J. Crew Wool Woodsman Cap, $58, available at J. Crew.
Clockwise, from top left: Filippa K Chunky Hat, $99, available at Bird; Dunderdon Jesper Reversible Slouchy Hat, $38, available at Oak and Dunderdon; B. Son Knit Beanie, $59, available at Revolve Clothing.
