Everyone is really an individual when it comes to cold weather riding. I can tolerate cold OK for sports with less wind resistance, but with cycling, I am always the one who has the most on. I know you are supposed to feel slightly cool at the beginning, but I hate feeling that way. My first mile from my house is downhill. It is freezing when it is cool out. I do tend to layer more now than when I first started riding, but what gets me are the people I see riding with shorts on when it's 55 or even 48 outside. I like wearing knickers between 55 and 65. If it's that temp. in the beginning of a long ride, I'll wear leg warmers, so i can be in shorts later when it goes above 65. As far as the top goes, I usually have too much on, but I'd rather feel sweaty than cold. For temps in the fifties i usually wear a regular long sleeved jersey with a heavier hoodie jacket, or a lightweight wool jersey (feels like cotton) and my wind jacket. Lower fifties, I go to a mid weight wool jersey with a vest or wind jacket. Less than 50, a mid weight wool jersey and my hoodie or wind jacket. I have a Gore Tex rain coat that is really warm, too and a Go Lite jacket that i wear X country skiing. I have worn that a few times when I've cycled in the winter. I wear full fingered gloves below 58 or so, one pair for temps in the 50s and the other for really cold riding and mountain biking. I also wear a skullcap or headband when it gets below 55 or so. Wool socks, yes, light weight ones most of the time up to 65. I have woolie bullies for when it's really cold, but they are a little thick with my shoes. I also have booties. Don't laugh! I wear them at times when it's in the 50's, but definitely in the 40's.