winter wear, hmm i usually run a bit warm since i'm naturally insulated (fat). For the brisk 5am walks with dog it's usually boxer's & tee shirt (what i roll out of bed in) boots if snow is deep, if snow is low, slip on shoes are sufficient. The dog is only interested in <5 minute walks in the early morning. For daily outdoor extended chores: deer skin gloves, wool hat, dry boots, jeans & i choose to light layer the upper half so i can un button waxed cotton jacket and or flannel shirt as i warm up. if it's below 20 deg f I'll add scarf, flannel lined jeans, and wool liners to oversized leather gloves. The trick for me is keeping feet dry and warm. Head warm but not too warm, and the rest of the body seems to regulate to the temps.