Hobo-chic is kind of a funny concept. I mean, why would you want to look like a dishevelled, raggedy, listless street-sleeper? When's the last time you've walked past a hobo and said, "Oh my goodness, he's so trendy- I gotta have his clothes"? Yet somehow, the combination of an oversized sweater and a toque or knit hat of some sort have become markers for being hobo-chic. I guess there's something about the essence of the trend that embodies the homeless toughness. Seriously, do you think you'd be able to tough it out on the streets, even for one night? I didn't think so. And no, passing out on the side of the street post-St.Patty's day doesn't count.
P.S. I don't know what compelled me to ponder this, but if I was actually a hobo, I'd carry around a sign that would say something like, "Nothing good to say. I just like signs" or "Made ya look!"