Seeking Very soft sole shoe advice

[KennethSime]

I'm with Riverkilt on the barefoot stuff, but I totally understand that isn't your bag.

A cursory search for orthopedic dress shoes turned up these guys from Dr. Comfort.

I'm not an expert when it comes to shoes, nor highlandwear, but I do definitely understand how hard it can be to find a good pair of shoes. Here's one other vendor who seems to stock a lot of orthopedic shoes. While I agree with the others that any shoe that works for you will be just fine, I think you'll look best in something approaching a leather dress shoe if it's at all possible.