Sometimes I think shoes are the most salient part of a person's outfit in terms of what their clothing choices say, but this probably depends on how a person feels about shoes...some folks think of them as pretty utilitarian, an afterthought, and other people just may not have the cash to buy the shoes they'd like to have, and while that may say something, it doesn't say a lot. Shoe-loving people with a little disposable income are maybe more likely to reveal something by their choices.
Earlier this evening I saw a lovely young lady attending a school function, and she chose a dress that was too short and stilettos worthy of a Vegas stripper, but I think she was just trying to look grown up. Probably some people will think she's trashy, though, poor baby.
I confess that although I am a cheapskate and haven't spent more than 30 bucks on a pair of shoes in a really, really long time, I love them and have too many. I have to dress conservatively at work, but I let my goofy streak show in my socks and shoes sometimes. I just bought a pair of these:
I'm not sure what they say, but they met my criteria by being funky and $14.99 on sale.