My problem with hush puppies and with many flats is that the back curves in too much or too tightly? I guess I have a flat back of my foot. But at least on amazon or some shoe sites you can browse the shoe from all angles.

I had a great pair of Sas penny loafers that I wore the feck out of and they never wore out. The penny part was very low on the toe, not way up high on the instep, so they looked more classy than preppy.