He learns something of the comfort of the bear in hibernation. The snug fit of most leather hiking boots can limit the circulation of blood in the foot. Especially with thick socks on. Overboots cut generously enough to hold your foot and shoe are much more effective. The cloth stitching in leather boots can also wick moisture into the shoe.
Nothing is worse that wet feet in cold winter.
To keep warm, in the cold, your clothing must allow body moisture to escape. Moisture that is trapped too close to the body can wick heat away through evaporation. It is better to layer your clothing on in cold weather. Wool, Gor Tex, and polypropylene garments work nice in the cold. Always wear insulated underwear.