Here are two rules of thumb that I'm heard about winter riding: First, if you're warm enough during the first 10 minutes on the bike, you're wearing too much. Second, ride the temperature. Meaning don't do any more miles than the temperature.

I think there's truth to each rule. I definitely don't like being too warm. First off, it's just uncomfortable and, second, it's no fun to ride in wet, sweaty clothes. That's why I like wool as a base layer. As for riding the temperature, I find that anything more than about 30-35 miles when it's cold and/or windy is just too exhausting. I like riding through the winter, but when it stops being fun, I try to ease back and do something else. I don't want to burnout.