No reason to stay dry. Just stay warm. Many knit layers. I'd run a silk base layer, arm warmers, ss jersey, and LS jersey to stay warm down to about 20 degerees (or 32 raining). Same thing with leg warmers and 2 pairs of tights if needed. Calientoes under booties are magical in really cold or wet weather.

I can't stand wearing a shell unless 15F or less.