An employee at REI asked me that the other day.
I told the guy that I wanted a light weight, sturdy shoe, because I was going to be backpacking around towns and cities for a long time, and I didn’t want to lug around a heavy and bulky pair of shoes.
Guy: So you’re gonna be a hobo?
Me: Am I gonna be a what?
Guy: A hobo.
Me: Oh, haha (fake laugh), hobo, yea, I guess…
I guess we Californians automatically assume anyone who is walking around town carrying a 40L+ pack on their back is a hobo.