Thanks for the interesting responses! I looked up hobnails and caulks and it appears that a woodsman would be wearing either of those but would still have to attend to dressing and drying the boots very frequently. I suppose campfires also were for drying socks and boots as well as heating coffee.

I've read that the Apache had a dual-mocassin system where they had very soft inner slippers used like socks covered with much rougher duty footwear and leggings.

The country I'm hiking in is shortgrass prairie with short cacti and rattlesnakes. It's noplace to be barefoot if there is a choice. (no rattlesnakes about on a a snow-muddy day though)
It's really not even a sound idea to wear fabric boots due to the cacti.

We sure have it easy. My boots are all dry thanks to my Peet boot dryer and the boots being mostly synthetic materials....