I survived some (read: very little) riding last winter wearing mostly street clothes - cheap henleys and T-shirts, a C9 jacket from Target (bought at the end of the season for $12), and jeans.
This year, I want to try riding more. So far, I've been ok, but I know Chicago is going to get chilly.
My biggest cold problem is my feet/legs. I'm thinking about picking up some leg warmers to go under my jeans, something like the cheap Nashbar branded ones. Are they going to be good enough to keep me warm? Even if my jeans are rolled up? Also, what socks do you all wear to keep your feet/toes warm? I'm going to be wearing street shoes.
The only other cold weather problem I have is a snotty nose. After 5 minutes, I basically can't use my nose. Any good way for combating this?