The older pair is soft kid leather with detailed stitching and perforations. Metal eyelets for the skinny laces. There is a mark on the underside, perhaps where a price tag was removed and took a very fine layer of the leather with it. This pair looks like 1930s or 1940s to me.The sole is slightly stiffened, like a layer of cardboard, but not as stiff as the leather on the other pair. These are about 4.5"  long and 2" wide at the toe.

The newer pair is a classic style, from the 1950s on. Fresh white laces, and they look like they've had white polish applied as well. Thick leather sole. They are 5" long and 2.5" wide at the toe.