Boot design commission for Attack1942 ( https://www.furaffinity.net/user/attack1942 ), showcasing a general-issue duty boot design for his 'Gilbert Consortium' military unit. Featuring leather and armour plating, the boots are designed to be compatible with a variety of species to maximise deployment efficiency.
This is probably the closest I have: https://inkbunny.net/s/394190 not a historic progression like you suggest, but I have at least dabbled in paw-wear types from different periods and settings. All of these are in my gallery individually if you want to see them full size. I certainly haven't done every possible thing, but I'm always a fan of interesting paw-wear designs with a long history of drawing it myself and enjoying it in others' art!
This is probably the closest I have: https://inkbunny.net/s/394190 not a historic progression like y
