I tried articulating some of this to some friends recently. I came off as elitist and nostalgic and sympathetic for Rockefeller types In college I had a class where an older gentlemen was taking a course for fun along with us kids. I did not know he was a wealthy alumni until it came out one day during discussion well into the semester. This guy dressed in cargo pants and t-shirts (surfer brands, Fitch etc) every day and always had earbuds hanging on his neck. I thought: there is no distinction, nothing that us college kids can aspire to in the most unaffected, basic sense of the word, once we presumably grew up and graduated if this guy looked like that at his age as a wealthy man. Here you find one reason for the dressing down phenomena: some see dressing sharply as establishment or elitist and it consequently elicits distrust. It is tied to the inverse snob.