Aren't these shoes incredible?!?!?! I just love the boldness of them. I believe they belong to Leighton Meister from "Gossip Girl". I could be wrong. But I love them, regardless of who is wearing them.
I would wear them with a 40's-inspired tweed suit, maybe in gray or black. Or perhaps a dove grey short suit. Or a purple jersey wrap dress. And, of course, with jeans.
I actually have a pair that are shaped like these, but they're solid black patent. I got mine at Target. They're by Isaac Mizrahi for Target. I purchased them several years ago but I still wear them all the time. Believe it or not, they're not all that uncomfortable and they can go with almost anything.