Hat Tricks

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.

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.

Because there really is nothing worse than the look of a guy who is trying too hard—you know exactly what we're talking about—we've chosen subtler styles, from clean and cozy knit caps to the most classic wool fedora (one that doesn't look like it was plucked from a stall on Canal Street). You'll know you've got the right one when you put it on and it looks like you've had it for years and years. Check out our favorite mix of options, and with price-tags starting at $32, this is one wardrobe staple you can afford to splurge on.

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.

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.

15+ fall toppers for the fellas.