Dressing for Winter

Phillip Stern

Many people stay indoors on their trainers when it gets cold. Not me. For years I bike commuted through the winter. Now I work at home, but go out for long rides on the weekends, year round. 

The main issue is safety.

  • Watch out for ice. Especially if snow melted the day before, the water can freeze overnight and make black ice along the shoulder of the road.
  • Wear colorful clothes, reflectors, and use blinky lights. The angle of the sun in winter can make it hard for drivers to see a cyclist riding into the sunrise or sunset.
  • Have the right clothing. Cold fingers, toes, and/or ears can ruin a ride. Winter specific cycling shoes, ski gloves, and a balaclava solved my frozen extremities problems.

For years, my problem riding in cold weather was that I dressed for the day before. If I was cold the day before, I wore more layers. If I was hot the day before, I wore less. As a result I was almost always over-dressed or under-dressed for the current day. Then a Ripper friend shared this “Winter Layering Done Right” page from Bicycling Magazine, and it totally changed my winter riding comfort.


The article was the starting point for my own personal layering guide based on temperature. After each ride I refined my guide, adding or removing gear as necessary for the temperature that day. Now my guide is so accurate that I check the weather and put on exactly what is listed in my guide and am almost always comfortable even when doing a 200k in January. I encourage you to make a similar personalized layering guide for yourself. Photo is author dressed for winter riding.













The author laid out his winter clothes for a better view of what it takes to ride in winter cold.

Phillip Stern is a CRW member living in Winchester.