I currently have three pairs of shoes that I rotate between (Allen Edmonds McAllister, Magnani boots, and White's Bounty Hunters). I want something slightly more casual, but along the same style (i.e. I don't want to wear sneakers). I want to be able to wear the shoes just about anywhere. Would my best option be penny loafers or is there some other shoe that would work for me? Also, is there a huge quality difference between getting loafers from Quoddy versus Alden? In other words, is the cost increase worth it?
Sounds like you need some chukkas. Alden unlined are my favorite.