I usually go with a poly-something base layer, a shortsleeve jersey, a long sleeve thernal jersey, and then my windbreaker jacket on top, and thermal leg warmers and regular padded shorts on the bottom. I have a pair of neoprene booties that I haven't used much as I mostly only ride in the cold for commuting where I'm wearing running shoes over wool socks, but I would use them on a road bike. I also have neoprene gloves which I find to be worthless on the bike. My hands get clammy and they don't keep out the wind. I also have a pair of PI fingered gloves that are a bit better but also lightweight. If I go out in very cold weather, I'd use my ski gloves, but I rarely do. I've tried a wool beanie under my helmet but found it uncomfortable, I haven't figured that one out really.

In the end, my feet still get cold, my hands are OK except that I have a nerve thing going on in my left hand and the cold makes it hurt. My head doesn't get cold, but a lot of my body heat is escaping that way.

I prepared for winter this year by getting my indoor trainer gear upgraded, with sensors and software, and at the end of the day I have a better idea of how I'm doing. I've been measuring my cycling in miles all these years, but watts is better. It makes me want to get a power meter, but they are expensive.