Previously, I'd always worn a wicking baselayer shirt and long, insulated running pants, then an acrylic sweatshirt that I'd cut the sleeves out of, then a waterproof/breatheable jacket and PVC rainpants on the outside...
Working at TE has encouraged me to... uh... set my sights a little higher for this winter. My shoppinglist included the Showers' Pass jacket (very visible, very, very breatheable) the PI AMfib gloves, Sugoi firewall tights, pearl armwarmers (ok, didn't buy 'em from TE, but X had 'em and they were a little small for her...) I happened to come by a set of gore bike tights -the cross3 ones- and they look good, too. Insulated thickly in the front with windproof, water resistant stuff, and a bit thinner in the back for flexibility. Woo! :) I'll probably need more insulation up-top when it gets *really* cold, so the sugoi tops that were mentioned earlier would probably fill the bill.
hope that helps. In all honesty, it's about what you're willing to endure. My running pants/pvc rainpants combo was wet on the inside by the time I was done with my hilly 10mi commute, but it kept me warm. At that time I wore leather boots and had flat pedals, so now I'm going with some kind of shoe covers to make up for having the clipless system now...
Ihighly suggest good gloves, though. My Nashbar neoprene gloves sometimes left my hands so cold that 3 miles into my ride back (still being wet from my ride in) I'd have to pry them off stiff fingers and blow hot air over them just to get them mobile enough to shift again. Not fun.
