I just started to ride in August of last year. Fell in love and continued all winter long. I'll start at my head...I have a lightweight ear band that was essential. I never needed a hat but the earband fit well under my helmet. In extremely cold weather, I wore a neoprene half face mask. It covers my nose and chin and has holes for breathing. Always wear sunnies...it helped keep the glare down and protects my eyes from wind, snow, etc. I wear a polypro long sleeve shirt, a cotton turtle neck, a wool sweater and then either my Goretex jacket or my North Face wind breaker. Legs...polypro long undies, my cross country ski leggings. I wear polypro sock liners and then heavy socks. My toes ALWAYS get cold. Haven't found a way to protect them yet. On my hands I wear a thin glove liner and then depending on how cold it is I wear the appropriate thickness of glove. They too always get cold. Now, if you are picturing this, you can imagine I am anything but an ad for cycling wear but I was able to ride ALL winter long! Hope you hear from others on how to keep your toes and fingers warm! It was invigorating to ride in the really cold weather. Watch out for your water bottle...it will start to freeze pretty quick!