In the comments to the last post, spectator shoes were mentioned. This Summer I have a pair, but shoes like this are best used sparingly. While it's true that the best spectator shoes are of the wing tipped variety, I find that casual loafers are far more easily wearable. While wing tip spectators do look good, they tend to come off as 1930s fetish/costume, whereas loafers are a bit less dated.
Here's an unusual pair. Split toed, brown leather and tan mesh, with a stretch gusset across the top. Really well made, a pair of "Freeman's Fashion Built" shoes. Homework tells me little about Freeman's shoes, other than that they were made in USA, and they faded into the distance in the early '90s. A perfect cinch with grey tropical worsted trousers, tan socks, and a white tennis shirt.
Extreme belt and shoe matching is accomplished with this braided cotton tan surcingle belt.
Both shoes and belt were purchased for resale at the last Top Shelf Flea, but I got hooked and I couldn't let them go. They fit me, and they were irresistible. It couldn't be helped. Such are the dangers of a life in second hand haberdashery.
Frank Lopez told Tony Montana through his girl Elvira that a big rule of being a successful pusher is "Don't get high on your own supply".
Rules, however, are fairly meaningless if you don't break them occasionally.