Condition your feet by going barefoot as much as possible during the warm months. Walking on paved roads is great for this. I can remember going barefoot pretty much all summer as a child.
Daniel Boone and his group took after the Indians that kidnapped his daughter and the Calloway girl from the Kentucky River. Traveling up Howard's Creek, Boone and his group tracked until dark and encamped. One of the men returned back to their home for the purpose of getting the mens moccasins. They had ran the entire day without any footwear.
I know an ex military man named Gary Barker and he would go on an 18th Century trek barefooted. We traveled some rough country and cold weather, but he never wore shoes. He carried a bare of brain tanned deer skin mocs and would occasionally wear them.
Point is that light weight mocs are worn as an added protection from briers and rocky ground, but you should be able to go bare footed first with out any trouble. The thicker elk hide and a wool liner is very much doable for tinder feet like me. The first time I ever wore mocs was a trip into the Virgina mountains and I wore only the mocs. By the next day I was hobbling around with severe pain. I located a fallen maple tree and cut squares of bark from it, then shaped them to fit my foot. The inserts were great and I got two days of wear before the bark split apart and needed replaced.
Heavy tanned cow hide is a great protection to the feet and a company named Carl Dyer's Mocs can supply them or at least show some great examples of construction.
