Go-To Winter Cycling Caps and Hats

Nowhere is winter more cruel to an intrepid city cyclist than to the extremities, with the head and face perhaps most vulnerable. After all, you can completely cocoon hands and feet, but above the neck the need for unobstructed vision and breath opens the door to wintery drafts and discomfort.

Here, we feature 10 head coverings, ranging from classic winter cycling caps to the helmet-and-chapka combo shown above, to keep you toasty and looking great on your winter ride.

When shopping for hats, caps and balaclavas, look for cold-busting fabrics that also help manage moisture — yes, you’ll sweat, even in the cold. Good choices include stretchy nylon reinforced with a wind membrane such as Windstopper® and the classic favorite, Merino wool. Caps with visors help shield eyes from wind and snow. In addition, some winter cycling caps feature handy fold-down flaps for ear protection.

The degree of warmth and layering you’ll need depends on individual preference and on the mercury reading outside. Here are the ranges of cold-weather layers to consider as temperatures plunge:

Low 50s to low 40s: From helmet only to light cap beneath helmet

Low 40s to low 30s: From helmet and cap with wind cover, as needed, to balaclava or neck gaiter

Below 30: Skull cap, helmet cover, ear coverings, balaclava or gaiter. The hardiest of riders sometimes opt for ski goggles in extreme conditions.

Whatever your winter cycling challenge, there’s a cap to help keep your ride comfortable.

Make it basic:

Tough Headwear Skull Cap – This basic, economical accessory, made of polyester and spandex with a brushed lining, is available from many different makers. I favor an ear-cover style like this one over a simple skullcap for fit and coverage under a helmet. $10.97

Make it merino wool:

45NRTH Greazy Merino Wool Cap – For protection and warmth, this breathable, cap constructed of double layer Merino wool, adds a brim and full-coverage ear flaps. $45

Make it waterproof:

Sealskinz Waterproof Cycling Cap – A water- and wind-proof outer barrier keeps your head dry, while a mesh lining helps manage perspiration and prevent overheating. $39.95

Make it full-coverage:

Pearl Izumi Barrier Balaclava – For the hard-core commuter, nothing banishes the cold like a balaclava. Special features: The forehead panel is the forward guard of wind protection and water resistance. A movable face panel lets you cover up when winds turn bitter, then pull down easily for temperature regulation. Reflective stitching and logo on this polyester capper help lend night visibility. $35

Cover your helmet:

Gore-Tex Helmet Cover – This one wins praise from reviewers for a universal fit, thanks to a gathered elastic hem, across helmet sizes, without flapping on smaller helmets. Waterproof, windproof and high-viz. $49.99

Top: Casqu’ En Ville Carbon Helmet and Chapka Cover, $137

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