I've always run wool as a first layer, most often Filson heavy weight depending on temps. Next is usually a berber fleece vest with a windproof liner or a Filson 24 oz wool vest. When really cold a wind proof hoodie goes over the base layer. Last is an outer layer that is wind and or water proof, and insulated.
i am a recent convert to vests. I swore them off in the apst due to my concerns that my arms would get cold, but after using one this year over just a base layer and wool shirt im sold. i will probably invest in one of the Sitka fleece vests. and add a Sitka heavyweight hoody. while keeping my puffy jacket and raincoat in my pack as an outer layer for sitting.
I bout a pair of puffy pants as well and wear them over a heavyweight waffle fleece baselayer and fleece pants the search for good boots continues