When did homeless become fashionable?

There is a guy in my office who I am sure is on the cutting edge of fashion. He has the messy hair, never clean shaven but never has more than a five o’clock shadow (I would love to know how he pulls that off) and he has the really cool “notice me” frames for his glasses. But I want to buy his ass an iron and a mirror. Every day he is sporting a sport coat that looks like he found on the side of the road and his shirts must have been wadded up in the pocket of said sport coat. And his shirts are never tucked in, but really what would be the point. But when did lazy slob become fashion? I should embrace this “trend” so that I could get more sleep at night.