Sombreros

Cycling headwear splits cleanly into two jobs. Summer caps — typically worn under helmets or alone on casual rides — are about sun protection, sweat management, and aesthetics. The classic cycling cap shape with its short brim serves both purposes well: it keeps sun out of your eyes on descents and soaks up sweat before it reaches your face. Winter headwear is a different calculation entirely. Once temperatures drop, ears, face, and neck become the first places you feel the cold. Thin skull caps fit under a helmet and add meaningful insulation without bulk. Face masks and balaclavas extend that protection when temperatures drop further, and on wet winter days, a windproof or water-resistant outer layer makes a real difference over a standard knit cap.

RA Cycles carries cycling headwear from Assos, Giordana, and Giro. Assos anchors the premium cold-weather end — their Winter Face Mask and Ultraz Winter Face Mask are purpose-built for serious cold and rain, with the Ultraz version stepping up the insulation for genuinely harsh conditions. Giordana covers summer caps thoroughly, with a wide range of mesh caps, solid-color caps, and limited designs like the Brooklyn Rasta and NYC Liberty that lean into the brand’s New York roots. The Assos Endurance Cap and Summer Cap Foil round out the warm-weather performance options.

Headwear pairs naturally with the rest of your cold-weather kit. Cycling gloves cover the hands when temperatures drop, and warmers take care of arms and legs. For the full picture on cycling apparel at RA Cycles, browse men’s cycling apparel and women’s cycling apparel. And if cold feet are the issue, the cycling socks collection includes insulated and weatherproof options for winter riding.