Northwave Extreme RR GTX Cycling Shoes$265 2 of 7
Photo Courtesy of Northwave
At first, we were skeptical about wearing just a pair of socks—without shoe covers in sub-freezing weather—with the Northwave Extreme RR2 GTX Cycling Shoes. However, just thirty minutes into a ride, with snow still melting on the side of the road, our tester remembered he was wearing minimal layers, and his toes were not cold.
These Northwave cold-weather cycling shoes, with an over-the-ankle Gore-Tex neoprene cuff, are plenty voluminous, allowing for thick socks. The carbon composite sole is also stiff enough while the SLW2 retention system is so easy to operate and provided a secure feel, even when climbing hard out of the saddle.
Specialized Therminal Alpha Jacket$200 3 of 7
Photo Courtesy of Specialized
The Specialized Therminal Alpha Jacket proved to be perfect for cold days when we needed extra protection. The Polartec Alpha lining is not only plush but also a great low-profile insulator, slipping on easily under outer layers. Two front zip pockets allow for easy access to a few items, like your phone, and the svelte hood fit easily with a helmet.
The Therminal Alpha jacket is just casual enough that it can even be used to commute to work on top of street clothes.
Rapha Thermal Bib Shorts$235 4 of 7
Photo Courtesy of Rapha
A premium chamois—the same one that's used in summer-weight shorts—is sewn into the Rapha Thermal Bib Shorts, and it's memorably comfortable. But contact-point comfort is not the only notable feature of this premium winterwear; the super-smooth Rapha Superroubaix(R) lining, unnoticeable flatlock stitching and straps that moved with our tester's body, made these shorts worth the splurge. When Paired with Rapha's Classic Thermal Knee Warmers, we were warm and comfortable on crisp, dry days.
Castelli Transparente 4 Jersey$169 5 of 7
Photo Courtesy of Castelli
Don't be fooled by the name: Like a form-fitting winter jacket the Castelli Transparente 4 Jersey kept us warm on near-freezing days. The breathable rear shoulder panels, super-easy pulling zipper and wind-stopping front panels had us reaching for it over other jerseys in our closet. This Italian-made outerwear is available in four different colorways, sizes S through 3XL for men and sizes XS through XL for women.
Pearl Izumi Elite Thermal Wool Sock$20 6 of 7
Photo Courtesy of Pearl Izumi
On cold days—even when wearing winter cycling shoes—warm socks are a must. The Pearl Izumi Elite Thermal Wool Socks with Merino toes and heels will keep your feet especially toasty. The stitching on top of the toes and the mid-calf rise help make these winter woolies a go-to cycling item.