We love winter because of skiing. But winter hats are a close second. From standard beanies to stylish brimmed lids to classic military tops, here are our favorite picks from the season.
Yellow 108 Luke Fedora ($90)John F. Kennedy might have killed the standard fedora by not wearing one to his inauguration, but we’re bringing it back with the Luke, which provides plenty of warmth thanks to the 100 percent wool body. The salvaged leather tie around the crown is a nice touch.
Flylow Revival Pom Beanie ($28)Flylow commemorates some of the best extinct ski areas—including Berthoud Pass (Colorado), Brodie Mountain (New York), and Slide Mountain (Nevada)—with its Revival Pom hats. Available this fall.
Stormy Kromer Peninsula Cap ($70)The classic Stormy Kromer cap (right), born from blustery Wisconsin winters, lets you slide the headband down over your ears when temperatures drop. This version has the classic red and black wool outer and a Horween leather brim. Also pictured: the Original Cap with Harris Tweed ($60).
Dale of Norway Cortina 1956 Beanie ($70)The Cortina pattern appeared on the Dale of Norway sweaters that country’s athletes wore to the 1956 Winter Olympics in Cortina d’Ampezzo, Italy. The outer is a warm, robust Norwegian wool, and a merino liner prevents itching.
Bailey 25135 Garren Pilot Cap ($200)Pilots used to wear caps like the Garren to keep them warm high above the clouds. Made from leather, cotton, and shaved lamb fur, the hat features earflaps that fold up on warmer days and down when the snow starts to fly.
American Trench Watch Cap in Superfine Merino ($85)American Trench upgrades the traditional watch cap, made famous by navy sailors, by knitting it from the softest, stretchiest merino you can find. This hat goes with anything.
Otis James Nashville Brawler Driving Cap ($140)The Brawler, handmade in Nashville, Tennessee, uses a wide-wale cotton corduroy for heat retention, and the six-panel fit sits at a just-rakish-enough angle to channel Newsies without becoming a full-on period piece.
Buff Knitted and Polar Slouchy Hat ($29)By far the most relaxed hat on this list, the Slouchy fits just as you’d expect: with the extra material on top bending down toward your back. The outer is acrylic, but the fleece lining will keep you warm even when it’s brutally cold.