The hat was a ruse! This is actually a painting of famous Hobo King Pennsylvania Kid Wilson, who being from Pennsylvania, was brought up wearing stupid hats.
I know I've told you before about tell-tale signs and that a large-brimmed hat usually means it's not a hobo, but here's the exception to the rule.
And to be honest, the brim isn't really as pronounced as the last Hobo Or Not A Hobo, it just looks like it. This type of hat is used as much to gather wind against the forehead as it is to keep the sun out of the eyes. With this type of hat, you catch even the slightest breeze and dry the ironhouse-of-freedom-born beads of sweat
So given that bit of trickery, how were you supposed to know that this was a hobo? Well, if you'll notice, Pennsylvania Kid Wilson isn't looking at the artist, he's looking behind him. Presumably because he's looking at a sculpture that he is going to use to smash over the artist's head when the artist lets his guard down.
The second big clue was all of the buttons on the overalls. Hobos love flair! And not just on the overalls, check out the zazz-laden hat full of clothespins.
This one really shouldn't have been that difficult.
But I do thank you all for your terrific guesses and dances with logic--even if they left you standing by the punch bowl.
Better luck next time!