In the winter, I almost always go the spaceman route: I wear long-johns, wool socks, heavy pants, and boots/spats for my legs. A t-shirt with multiple sweaters/flannels, a fleece, and a rain-jacket with pit zips for my core. I cap the "spaceman suit" off with a hat, helmet, googles, and nylon gloves inside of leather work gloves. You'll know if you've dressed well enough, because riding will still be fun.