Male Fashion Advice

I don't have any brand recommendations, but you're probably going to be looking for a pair of Goodyear Welted shoes. There are plenty of other construction techniques, and not all goodyear welted shoes are high quality, but there is a strong correlation between it and quality.

Aldens are pretty highly regarded for quality. People seem to like Grant Stone as well. I don't own either, but I have a couple pairs of Rancourt & Co and love them. A few years ago they were doing at cost sales of limited styles, so if you're in no hurry it might be worth getting on their mailing list and seeing if any more come up.