I happened upon a fun article discussing some winter riding tips published by Pete in Ottawa, you can find the entire article here. Even if you aren't into winter cycling, this article is entertaining enough to warrant a quick read. Here are some of the highlights:
"Something I like doing in the winter is to buy a Popsicle before I leave, and put it in my pocket. It won't melt! I take it out and start eating it just as I arrive at the University. Its fun to watch peoples' expressions when they see me, riding in the snow, eating a Popsicle. You have to be careful with Popsicles in the winter. I once had a horrible experience. You know how when you are a kid, your parents told you never to put your tongue onto a metal pole? In very cold weather, a Popsicle acts the same way. If you are not careful, your upper lip, lower lip, and tongue become cemented to the Popsicle. Although this sounds funny when I write about it, it was definitely not funny when it happened."
"Starting at the bottom, on my feet I wear Sorell Caribou boots. These are huge ugly things, but they keep my feet warm. I have found that in extreme to insane cold, my toes get cold otherwise. These boots do not make it easy to ride, but they do keep me warm (see rule 2, brute force). They do not fit into any toe-clips that I have seen. I used to wear lighter things for less cold weather, but I found judging the weather to be a pain. If its not too cold, I ride with them half unlaced. The colder it gets, the more I lace them, and finally, I'll tie them."