Yeah this screams of this one site that I see adds for all over the place. Not sure what it's called but the style is similar. It's a fun idea though so maybe a different approach is needed is all.
The concept really makes no sense to me at all. Maybe it's an American thing. The style is extremely cliche for the retro looking shirts. (which if you look at the Threadless catalogue, you'll notice there are almost zero retro looking shirts) It's executed alright, but it looks a bit cheap and something you'd see at a bargain store.
About my design