I think dry is most important. Wet will suck the heat out of your feet no matter how fancy your boots are.
Take a load in a creek, getting dry again is an important thing. Dry foot, dry sock, plastic bag, on with the wet boot.
With my long narrow feet, I have to make certain that the heel rises with my foot so I don't get friction blisters.
For that, the old Greb Kodiak Classics really did fit my feet. But, I guess it's live and learn.
We've done rather well what with oil patch workboots to -60C. Mine are great, barefoot, at -20C. They're just 2-part snowmobile boots.
Between that and Carhartt clothing, most outdoor construction here still goes at -25C.
I had a pair of moose-hide mukluks made for me with double soles. Knee-highs with thongs.
Felt insoles and ordinary socks were just fine for a 1/2 mile walk to university at -20C, the snow is like sugar.
Never tried them with my 60" trailbreaker snowshoes. The loose, sloppy fit is nice.