Eskimo-approved, the trapper-style hat is the coziest of all. And whether you take the posh or the affordable route, one thing’s for sure: You’ll stay downright toasty. From top: Dolce & Gabbana's fox fur trapper hat, $3,895, at Dolce & Gabbana stores, 877.70.DGUSA, dolcegabbana.it. ; Tory Burch’s rabbit fur hat, $495, at toryburch.com; J. Crew’s shearling hat, $195, at J. Crew, jcrew.com.
The French have taught us a thing or two about fashion, and the tres chic beret is just one example. But fashionistas be warned, these lightweight lids are best on not-so-blustery days. From left: Eugenia Kim’s purple wool beret, $198, at Intermix, intermixonline.com; Coach’s pink wool beret, $148, at Coach, coach.com; Kate Spade’s wool beret, $95, katespade.com.
Sometimes a ski hat just won’t cut it. So for those more formal evenings out, this elegant number will turn heads—while keeping that of your own nice and warm. Fendi’s fox fur hat, $1,720, at Fendi boutiques, 800.336.3469.
Perhaps the most versatile hat to be had, a knit beanie is just as appropriate on the city streets as it is on the slippery slopes. And with so many playful options out there, one of these caps is certainly not enough. From top: Missoni’s mohair knit hat, $225, at Intermix, intermixonline.com; Banana Republic’s wool and cashmere cap, $49, bananarepublic.com; Miu Miu’s wool hat, $120, at select Miu Miu boutiques, 888.977.1900.
Known for his super-soft cashmeres in bold designs, designer Lucien Pellat-Finet has one-upped the basic beanie with this cheery topper. Consider the blooming buds a reminder of what’s to come after the thaw. Lucien Pellat-Finet’s cashmere cap, $506, at Lucien Pellat-Finet, New York, 212.255.8560.
A modern take on the ones Mom used to make you wear, these casual knit toppers—replete with pom-poms and earflaps—are just as cute as they are snug. Perfect for building that backyard snowman. From top: Topshop’s cotton hat, $32, topshop.com; Adidas Originals’ acrylic hat, $24, at Adidas Originals stores, adidas.com/originals; Kate Spade’s wool hat, $115, katespade.com.