I was a boyscout. and we did a lot of winter camping and activities.
About those stockings, that would help more than you imagine, I used to have thermals that were similar, and you wear them under something loose, but not baggy, with another layer over it. the theory is that it traps warm air between layers.
-Cotton Kills- it traps the moisture inside it.
You want to avoid sweating, that's why you wear layers, so you can adjust to extra heat you make by working, and the normal changes as the day progresses
Wool will keep you a lot warmer when wet that cotton will.
Synthetics dry out faster and tend to be warmer than most other options.
You do want something dense to stop the wind, a lot of synthetics let the wind straight through.
Never tried Goretex, but two of my scoutmasters swore by it. some of the earlier stuff didn't breath though.
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