I'm really on the fence about this guy.
While the H on the jacket may be screaming "I'm a Super Hipster!", the high school jacket from yesteryear and snarl on his face say "Retro douchebags shouldn't be messed with."
Regardless of what he is trying to say about himself, I'm pretty certain she didn't mean to wear a shirt that makes her look like she has the world's flattest, sagging pancake boobies this side of the equator. But maybe that's the look that people who wear white turtlenecks are going for.