When I was a kid, there was a show here in Canada named The Littlest Hobo. It was about an overly clever german shepard dog who was traveling and helping people on his way.
This design is not about the show but when I think of the littlest hobo, I always have that image in my head. Once again, had to get it out.
Would be better if the "hobo"'s head was partially overlapping the photographer's leg to give a sense of depth. Either that or add in light shadowing for scale/depth. And fix the photographer's left foot a bit. Otherwise, I'm from Canada and also thought this is what that show would be about.
This design is not about the show but when I think of the littlest hobo, I always have that image in my head. Once again, had to get it out.
Hope you like it.