It’s true: your head loses around 7 to 10 percent of your body’s heat—whether you’re spending winter nights in the desert high country or riding Colorado’s lifts—if it’s not well insulated. Still, though you should keep your dome swaddled, there’s no reason not to look good while doing so.
Snowshed 3-Season Helmet Beanie ($35)
Top of our list for high-output winter activities is the 3-Season Helmet beanie from up-and-coming Chicago company Snowshed. It’s made from fine merino wool and fits nicely into your pocket. We wore the 3-Season beneath our bike and ski helmets without any bulk, itch, or overheating, thanks to its thin profile.
Outdoor Research Whitefish Hat ($56)
For something burlier, Outdoor Research’s new Whitefish hat is a Stormy Kromer–esque utility lid with a water-resistant polyester outer and warm fleece interior. Even though the earflaps seem a bit goofy, we got over the look once we felt how warm and comfy they were. Snap them back for a dash of style.
Stetson Explorer Crushable Hat ($75)
Our favorite hat by a wide margin comes from an old-school company that specializes in making traditional western headwear. The dapper Stetson Explorer Crushable hat is 100 percent wool and 100 percent cool. The wide brim kept the sun off our testers’ faces, and, after an initial break-in period, the Explorer stayed snug and didn’t fly away in the winter wind.
Filson 5-Panel Cap ($75)
For the sports-fan-cum-hook-and-bullet-aficionado, there’s Filson’s 5-Panel cap, which blends the warmth of a beanie with the silhouette of a ball cap. The five panels—made of USA-sourced wool that naturally repels water—hug your head. If that hug is too tight, adjust the leather strap in the back for more breathing room.