Andy Moss
Daily Commute: 20 Miles Round Trip
Commuted Through Chicago Winters: 4 Times
Strategy: Don’t Sweat It

I grew up in northern California, but have lived in Chicago for nearly 25 years. By mid-January of every year, I still question what I am doing here.

My winter cycling wardrobe has changed significantly in the four years I have been commuting by bike, and has evolved by hit or miss. I prepared for my first winter under the assumption that I needed to be covered up and layered to the hilt. But over time I have reduced the number of layers I wear and lightened my load.

Several factors influenced what I now wear. First, I commute from Oak Park to the Loop, roughly 10 miles each way by the most direct route. In the winter, with my heavy backpack or panniers full of work clothes and books and stuff, and because of slower speeds due the cold and slippery conditions, and plentiful stoplights, my commute takes me up to an hour, or about 15 to 20 minutes longer than in the warmer months. Also, I face a headwind almost every day. Headwinds seem stronger in the winter, and certainly increase the wind chill on exposed skin and slow me down. Thus, I am outside for a long time, and avoiding sweat is my chief concern. Given the longer distance of my commute, riding deliberately slow is not a good option. Accordingly, I don’t mind feeling cold when stopped as long as I am comfortable while moving.


Here’s what I wore last week, starting with the bottom half:

Below 20 degrees, I start with a pair of regular Under Armour long underwear and a pair of wool cycling socks. I wear several different brands, but currently I like DeFeet’s Classico wool socks.

Over my long underwear, I wear one of two types of pants. My preference is Rapha ¾ Shorts, which on me equate to a cropped pair of cycling pants. I like Rapha’s ¾ Shorts because they are very durable, very flexible and reasonably warm. For wetter days, my preference is either Endura Singletrack or Endura Zyme ¾ Shorts.

For my feet, I wear a pair of Giro Alpineduro SPD boots. This is because I prefer clipless pedals in the winter. I switched to the Giros this year from a pair of Keen Springwater II shoes. The Alpineduros are extremely warm and completely wind- and water-proof, so only a single pair of regular socks is necessary.

Moving on to the top half, my first upper layer is a wool long-sleeve t-shirt by SmartWool or a wool long-sleeve cycling jersey. I have several wool-blend jerseys from Rapha and Road Holland. I like these a lot, and, of course, a Chainlink wool jersey! Over my first layer, I wear an Ibex Shak jersey. These two layers are a very warm combination, so if the temperature is likely to rise in the afternoon, I carry with me an Ibex Shak vest. Ibex sweaters are light, non-bulky, and wear really, really well.

I top off with a Showers Pass Amsterdam Jacket. This jacket is reasonably light, reasonably breathable, flexible and wind- and water-proof. It also looks like a classy herringbone wool coat.

Around my neck, I use a Rapha Winter Collar, and Rivendell’s late, great Possum Wool Gaiter over my face. I love this gaiter. It weighs next to nothing, it never smells, it feels really good on my skin, and it seems to magically absorb the wind. On my head, I wear an Ibex wool beanie under my helmet and over my ears. In the winter, I wear a Nutcase helmet because it is not well ventilated, and thus keeps the wind off of my head. I typically do not use a balaclava unless absolutely necessary. 

Over my eyes, I wear a pair of cheap motorcycle goggles with interchangeable lenses.

I protect my hands with a pair of Gore Tool Windstopper Soft Shell Gloves. I have been wearing the same pair of these for four years, so they are very durable. Glove liners are not necessary, although I carry a pair of thin gloves and several handwarmers in the event of a flat.

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