That looks like a good candidate for the mesh deform modifier and a mesh “cage”. The idea is to make a simple mesh that fits over the boot/shoe, then bind the pieces to that cage using the mesh deform modifier. The cage is then parented and weighted to the character armature to deform with the leg, foot and toe bones. All of the separate pieces will deform uniformly because they are all being deformed with the cage.
Good luck!
