Um, are you completely clueless? He's actually been employed in the fashion industry for many years and is a super humble dude. He's from SALINA, Kansas. Do you know how small of a town that is? He isn't some Upper East Side old money turd with a trust fund. He came from nothing, blue collar as it gets. He doesn't peacock around Pitti like numerous nascent bloggers. He's actually expressed confusion as to why people bother to take his photo so often and wishes he wasn't considered a "style icon." He just happens to be a handsome dude who understands how to dress well for his body type.
Face it, this whole obsession we have with expensive used clothes is escapism at its finest, we're trying to look as rich as we can on a budget. We are all more or less "herb".