What should I wear while winter cycling?

Wow, good question. But a complicated one. There are so many choices. How cold do you intend to ride in? Freezing? Around 20 degrees? Colder? Cycling is hard to dress for because you have wind chill at speed, then can easily overheat when climbing.

The Zephrr Jacket

Layering is the key. When it’s in the 30s, I start with a midweight long-sleeve jersey or top, such as REI’s Midweight Long Sleeve Crew ($30). Maybe throw a regular short-sleeve jersey over that for a little extra. Over that I like Pearl Izumi’s Zephrr Jacket ($75). Midweight tights such as the Louis Garneau Vello Thermal Tights ($70). And midweight gloves—I recently referenced the Manzella Silkweight Windstopper Gloves ($30) for a guy going to Everest, and they also are what I wear when it is chilly on a bike. Great gloves.

When freezing down to 25, I like a little heavier pair of tights—Performance’s Radiator ($60) are a great buy in a very warm tight. For a base layer, I swear by wool—Icebreaker’s BodyFit2 60 Crew ($80) is dynamite. Over that, if dry, the Zephrr. For gloves, maybe the Gore Bike Wear Mistral III ($50).

If it’s really cold, then a wool short-sleeve T under the long-sleeve T like Patagonia’s Merino 2 T-shirt ($65) adds a lot of warmth. A beefier jacket—the Showers Pass Elite 2.0 ($230), which uses eVent fabric so it’s great in the wet too. Pants? Pearl Izumi’s Amfib Tight ($100), which are windproof and lightly insulated. Pearl Izumi for gloves, too, their Barrier Lobster Glove ($70), which are waterproof and insulated.

I’ve biked in the low 20s with basically Combination Two. You’ll need to experiment a bit and see what works. Once you’ve got some trips under your belt, you can start to fine tune your gear in five-degree increments.