Looks like a cross between folk art, and revolutionary revival from the 1970's... There's a lot of that stuff around. I collect bicentennial memorabilia, among other things, and I see stuff like that at antique shops and thrift stores. Looks like something that I'd buy, just to aggravate my wife. I like it.
The poetic license of folk art . . . crude but fun.
The Tricorn/Cocked hat looks like it was painted by someone who had never seen one worn in person.
The US Flag didn't have rows of stars until 1795 with 15 stars - the "Star Spangled Banner" itself (there were some Navy Jacks before that but they weren't common).
One of those items sold at establishments flying the National Flag of New England.