There was this free fitness magazine published in San Diego that I would pick up at the smoothie shop or the sandwich shop when I saw it or when I thought about it. It usually focussed on 5Ks, 10Ks, half-marathons, etc, but every once in a while there were some articles and interviews about and with cyclists.
An article in one issue talked about an old timer who used to race around New York and Nre Jersey. I don't remember his name, but he was full of adages like, "Once you learn to rest while going up hill, then you'll be an effective cyclist." (Meditating on that quote lead me to change my jogging style.)
He also refused to wear synthetic materials and modern racing jerseys. In perfect contrast to fanatics today who are adamant about not letting cotton or wool be the layer against their skin, this guy said he always wore two long-sleeved cotton t-shirts. Once he sweat through the first one, then it would sweat through the second one. The layer against his skin was dry, and the outter layer kept him cool. He recommended this setup for both warm and cool weather.
I was thinking about him last night as I was riding home in mid-20 degree weather. I had been seeing people during the day walking around in huge winter coats, gloves and hats, and here I was, comfy and cozy in two long-sleeved t-shirts and a windbreaker.
This morning, I decided to test my fortitude and venture out with only one t-shirt and only one pair of socks. I made it, but sure wasn't comfortable at the other end of my 8 mile commute.
The main point here, though, is that you don't need a ton of fancy equipment or clothing in order to ride, or even to ride through the winter. Just layer up a couple of cotton t-shirts, and get out there on the road.