Shiny, structured penny loafer that won't cut my ankles, under ~$250?

Searched posts but didn't find exactly what I was seeking.

I'm not one to usually need help with this kind of thing, but I can't do Weejuns anymore. They look amazing but after a couple hours, my ankles are bleeding, back and sides. Needing something with the same vibe, but specifically more low-cut and more forgiving on the ankle bones and heel.

Sebago? Rancourt? Can anyone get a ruler and measure theirs for me? Don't feel like buying three or four pairs and sending them back. Thank you!