1. To be wise in the ways of the life in a large metropolitan area.
2. (Derogatory) (To be said of a stupid person) To know what street one lives on.
1. He's lived in Detroit all his life. He's very streetwise.
2. Matt's not completely stupid, at least he's streetwise.
Someone who can squabble, knows the slang of the street, and respects the "criminal world"'s laws
I'ma streetwise because of the place where I'm from