Just got back from a 32 mile hilly (short but steep rolling hills) ride. The outside temps were in the low to mid 30's.
Just switched over to my winter wheels (clinchers with 44X17) as the shoulders get crappier during the cold weather months. In the late spring through early fall I run tubular wheels with 44X16 but I am now working on my spin.
For the very steep stuff I traverse the road (traffic permitting) and gut it out. I run 2 brakes for safety but I am loathe to touch them if I can spin out the 70" gear.
FG riding will help keep you warm.

Good luck!