I wouldn't, but I am biased against hobos that way. They really strike me as a casual-only bag because they are so slouchy. It would look sharp with a pants or casual skirt outfit, but it would strike me as out of place with a nicer dress or even business attire.
But perhaps I am in the minority, as hobos are very popular. Maybe other people see them differently from the way I do.
But perhaps I am in the minority, as hobos are very popular. Maybe other people see them differently from the way I do.