I spent a small fortune on piecing together some winter riding gear in hopes that I would maintain my progress from last year. Actually, I picked up most of it deeply discounted from Bike Nashbar. Based on my first year attempt at riding in the winter - I wouldn't go out under 30 degrees personally. It gets super windy here too which just makes it unbearable. I wound up buying a trainer after thinking I would tough it out in the cold.

I have ridden in the 30s and 40s fairly comfortably this winter though. I resorted to using my thick hiking wool socks (some Smartwool)- my feet/toes get the coldest. I gather those heat packs work well for that. I bought some neoprene Peal Izumi shoe covers to help block the wind - they do work pretty well even though mine aren't insulated. I wear a balaclava from my motorcycling gear kit or a Pearl Izumi fitted cycling skull cap. I picked up a pair of Cannondale midweight thermal bib tights. A Cannondale thermal cycling jacket that blocks wind well. A regular Pearl Izumi four season full sleeve base layer and a thermal full sleeve base layer that I haven't tried yet. A Cannondale full sleeve winter jersey. Pearl Izumi winter gloves (these work better than expected - don't remember the model name off the top of my head). I also bought some Descente leg warmers that I've worn on days that I knew it would get warmer or that were not too cold to begin with. I've considered wearing them under the midweight thermal bib shorts, but I can't see me going out if it's that cold.