So here's my situation: I'm looking for business conservative dress shoes. I have bad ankles (surgery on one with recurring pain, history of sprains with the other) and wide, flat feet, so shopping for comfort is very difficult. Before I started my new job where I wear a suit and tie every day I found that Johnston and Murphy's shoes provide that comfort at the obvious expense of quality leather. The difference to me between them and a pair of Allen Edmonds, for example, is the cushy sheepskin soles and the wide cut of the shoe. After doing some research and looking around at other gentlemen in my office, however, I've realized that I would like higher quality and more conservative footwear than the loafers I currently own.
Today I went to AE and JM and tried a few pairs on. The only pair of AE that I tried on that felt moderately comfortable were the Bostons, which are not being made anymore (or so I'm told by the manager). They will definitely require that I throw in some cheap orthotics if I get them, since the leather sole is something that I'm not used to. JM had a nice monkstrap (callum buckle) but again, the quality was obviously worse compared to the AE (and only $50 cheaper).
My question is this: does anyone know of a monkstrap, oxford, or any other business conservative shoe that would go well with black, navy, toupe, and gray suits, that may fit my ridiculously difficult standards? Am I just missing something here? Because from what I'm reading it seems like AE > JM, but JM produces such a more comfortable shoe for me.
Of course, I would love to get something even higher in quality but $350 is my limit for each pair. I'm looking for both brown and black.
Additionally, any casual shoe recommendations are welcome (maybe a suede or wingtip while keeping in mind my "foot" issues).
Thanks in advance!