The shirt doesn't really fit the whole image you have going with the dark beanie, dark pants e.t.c.
I'd use a true hobo shirt if I were you. I wanted something like this while requesting a hobo set. I found that if it's made with proper texturing it looks really nice. Stains and rips would also be a nice addition to the general hobo image.
As for the feet, I'd recommend continuing the bandage. Not all the way, but something like a third of the way down the foot. Broken toenails, as well as blisters are typical on your average hobo. The bandage shouldn't look as if it's professional hospital quality, hobo's wouldn't have access to such high-quality products. Rather make the bandage out of second-hand rags. Not all the same color, the average hobo probably doesn't get to choose what color bandages he gets to wear.
Hands, same general concept, a makeshift bandage on the back of his hand covering up a small cut would fit nicely.
I would get rid of those anime eyes, they seem inappropriate as bostaff said. If you think about it, a hobo has been through a large amount of suffering, poverty, disease, and death rock this guys world. The eyes should really be more serious.
I like the way this is coming along though.