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Patagonia Snowfarer Cap ($39)
From backcountry laps to après beers, keep your cool in this brushed synthetic-lined flat-brim. The low-profile back clip and flat seams make it comfy under a helmet, and the 100 percent recycled nylon material is DWR coated to shed all the pow you encounter.
Simms Dockwear Insulated Cap ($40)
This classy five-panel protects from harsh winter sun and fends off flurries with burly waxed canvas. Its quilted polyester insulation and flannel-lined front panel lend warmth on chilly days.
Nathan Reflective Ponytail Beanie ($30)
On our first test run, we didn’t even notice this beanie’s ponytail hole, which, it turns out, accommodates even the thickest of manes. The light microfleece lining and snug fit were perfect for high-output activities, and the reflective detailing kept us visible.
Buff Merino Wool Fleece Hat ($35)
Two layers of Buff’s new merino fleece—a blend of 98 percent wool and 2 percent elastane that is stretchy, soft, and snug—make this lid special. It has all the warming, wicking, odor-resisting, quick-drying benefits of wool in a tight knit that keeps winter winds at bay.
Tentree Classic Rib Beanie ($35)
Tentree uses recycled plastic water bottles to craft its stretchy rib-knit merino and polyester beanie, which keeps you fashionably cozy whether you wear it slouchy or cuffed. Even better, if you register it online, Tentree will plant ten trees and give you a code to discover where they put down roots.
Flylow Barracuda Pom Beanie ($30)
When it comes to poms, we say: go big or go home. The Barracuda fits the bill, with an ample yarn topper that’s hard to ignore (a slouchy fit keeps things casual). We also love the super-soft, quick-drying acrylic that keeps you toasty no matter the conditions.
