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 cocoon hands and feet, but above the neck the need for unobscured 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 heartiest of riders sometimes opt for ski goggles in extreme conditions.

Winter bicycling in comfort and style? We’ve got you covered.

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

  • Shutt Velo Rapide Limited Edition Tweed Caps, $53

  • Smartwool Balaclava, $40

  • Fifo Cycle Blériot Hat, fits under helmet, $92

  • Under Armour Coldgear Hood, $25

  • Knit Liner for Women's Berkley Helmet, $39.99 (Helmet, $79.99)

  • Rapha Winter Hat, $55

  • Helmet Huggers, faux fur band around a spandex shell covers helmet, $48

  • Gore WindStopper® Bike Helmet Cap, $33

  • Ibex Merino Pace Beanie, $35

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