Florida native, now a resident of the northern Midwest, went for my first winter ride today temp was mid 20's, very little wind and the roads were relatively clear. Wore bike shorts, long underwear (old pair from my skiiing days), sweat pants, compression shirt, sweatshirt, light goretex jacket, gloves, glasses, and helmet. Went out for about 45 mintues did about 14 miles. I was shocked to find that I was very comfortable with the exception of my feet. I wore regular low rise cotton socks and midway through the ride my feet were freezing. Not sure how much winter gear I will invest in but one thing is for sure, I will buy some better socks! Next time I'll leave the sweatshirt at home also.