Lots of great advice given so far.
I usually wear this shirt which is made of heavy cordless corduroy under my leather pullover coat.
After that, if it gets colder, I slip this poncho over the coat.
My haversack carries all my fire starting supplies and other things that can be used in an emergency. Long leather laces, rope, knives, wool gloves, bandana, etc.
I wear just basic leather boots with good moisture wicking socks. As long as I'm on the move, or somewhat active, I have no problem with cold feet or legs.
Most of the areas I hunt, I've hunted for three decades or longer. I know the area's best water supplies, dead falls for shelter, natural blinds, etc. When I do go into an unfamiliar area, I am always trying to be aware of my surroundings. Remember where you seen that deadfall that would make a shelter, mark in your head, or map, where you last seen good tinder, what were those crows fighting about?
Keep in tune with your surroundings, learn basic skills if you haven't already, and you will stay comfortable.