St. George, I am working on my impression, based on my own great-grandfather, a veteran of the Third Wisconsin Cavalry. Mirroring his real life, he comes home from the war and plans to resume farming in Wisconsin, settles in, marries and starts a family, not far from the two of the three brothers who survived the war. Then it all goes to hell, a fever carrying off his wife and child within a few days of each other. He sells the farm, packs up his harnessmaker's gear, throws his trusty old McLellan saddle on one of his horse and heads out to start fresh, thinking he might find work freighting in the border country and the Indian Nations, where the Third Wisconsin hunted Secesh for the Union. He's no rabid Unionist, appreciating all who make their living from the earth and or with their hands. And he figures knowing leather, harness and horses will improve his odds of finding work. So he finds himself on the edge of the Plains about 1871 ...
He'll have boots very much like those he wore in service for horseback work, and a set of clothes for "town" and camp, as such -- hence the bootees to go with the pull-on boots.