The Yankee

Sketched this yesterday at work. This character is kind of difficult to nail down. I'm trying to find a balance between him being a pompous ass, and still managing to be accessible(sympathetic might not be the right word) to the reader. I also need to find the right balance between him being fashionably hip and attractive, but with an awkwardness that makes it all not really work. That sense that he thinks he's way more attractive than he actually is. And all this without plunging into caricature.