Westmass, you need to move someplace warmer. 35F yesterday. Put booties over my shoes. Wore Craft pants with windbloc front over my biking shorts. Put thin patagonia polypro underwear top under my normal short sleeve cycling jersey. Added a windbloc vest and put a shell over all that. Added a thin balaclava and wore gloves under my pogies. I could have left the pogies off but they'll just stay on my bike at this point. I was dressed perfectly. I unzipped my shell almost entirely after I warmed up. The windbloc vest is key for me. It lets me open up my outer jacket and get good air circulation without getting wind directly on my chest. Studded tires keep my ride slow as the old dog I am, but it was a good two hour workout.