As to how did the Indians keep their feet warm and dry ... too big for this thread. E-mail me if interested. As to boots, in very cold winter, I have hunted in well below zero and deep snow this winter, I wear a silk sock, with a good wool sock over that. I have a pair of Sorels a size bigger than my foot. With the extra socks it fits ok. I walk up and down hill sides, over ice covered rock ridges, side slopes etc. I have been warm and dry. They are heavy, but I am warm for many hours.
For fall and early winter, I like a light boot, even if it means being cold. Smaller is quieter. I have a pair of 17 inch boots from Cabela's. They are very quiet and the right one never leaks! My left foot hates those boots. Crossing creeks is always a bummer. I suggest a pair of wadders bigger than your foot size with moccasins inside. After the crossing, hang them upside down, and sneak in your mocs. I love hunting in mine.
Good luck man.
Bob.