Worth & Worth Aria Felt Hat

Come cold-weather season, style-conscious men have two choices when it comes to headgear: They can reach for a beanie (which is acceptable, if always considered casual) or don a hat. Like a hat hat, with a brim and made from rabbit hair felt (only beaver beats it for durability). Which is to say, of the timeless varieties worn by Messrs. Bogart, Sinatra, and famed archeologist Dr. Henry "Indy" Walton Jones Jr. (and not of the sort worn by pro athletes).

We see echoes of those classic styles in the Aria, a winter-weight, made-to-measure, 100-percent rabbit hair lid from New York milliners Worth & Worth. We pair ours with well-tailored suits and a three-quarter-length overcoat. W&W proprietor and head designer Orlando Palacios has a completely different take, however. "The Aria can be rocked with almost anything," insists Palacios, though he cautions that whatever you choose, refrain from cocking yours all the way back. "A little snap in the front, just above the eyebrows, is the age-old way," Palacios counsels.

Palacios says the Aria, like all his hats, is not only made with the finest textiles but, as a veteran designer and manufacturer for 20 years, it's also a product of love, sweat and, sometimes, literally blood ("we prick our fingers hand-sewing the bands," he says). We think they look all the better with a few stains and scrapes of hard use, so don't be afraid to wear yours in a snowstorm or even in the summer on the ranch. And like your fedora-wearing forebears, we'd suggest pairing one with the ultimate accessory: a sweet dame around your arm. [$275; hatshop.com]