Grow some hair. A beard is nature’s balaclava. Granted, most people are unable to grow one due to gender, age, or spousal disapproval. Let me tell you, though, a week or two of growth goes a long way towards keeping your cheeks and chin warm. Leg hair can be a big help, too, creating an insulating layer of warm air between your skin and your tights. Again, social mores and marital harmony may rule this out.
Get a hardshell jacket. For years, I piled on layers of undershirts and jerseys as the temperature dropped. I stayed reasonably warm, but felt a bit sausage-like under the compression of all those layers. This year, I bought a waterproof, windproof jacket (the Showers Pass Elite 2.0). Unlike a winter jersey, it has Velcro cuffs, pit zips, a vented back, and an elastic drawcord in the collar. As a result, I’m able to make mid-ride adjustments so that I’m never too cold or too hot. I can ride comfortably at temperatures between 20 to 40 degrees Farenheit with just my jacket, a short-sleeve jersey, and a long-sleeve base layer.
Don’t sacrifice circulation for insulation. As I mentioned above, I used to over-swaddle myself for winter rides. I’ve since learned that looser is warmer. Loose clothes allow warm, dry air to circulate against your skin, keeping you from getting cold and clammy. This applies to upper-body and lower-body layers, and especially to hands and feet.
Get some good lights. Around here, what little daylight we get during the winter is often lessened by clouds. A good set of blinky lights will make you more visible during the day, and a good set of rechargable lights will enable you to ride all night long (if that’s your kind of thing). I’m a big fan of DiNotte’s LED light systems. I have a 600L on my handlebar, a 200L on my helmet, and a 140R taillight.
Build a great indoor setup. I bet you thought this was some tough-guy article about riding outdoors all year long. Well, riding outside is usually better than riding inside, but not when death by snowplow is a possibility. The secret to endurable indoor riding is a good setup. For that, I recommend a fan, a big TV, lots of race videos and action movies, and a power meter (to keep you honest). Company can also be a big help. My wife’s treadmill is right next to my rollers. Instead of watching TV or a movie from the couch, we’ll head down to the basement and spend our tube time working out. It’s surprising how quickly a two-hour indoor ride can go by with the right distractions and a minimum of fuss.