@myfavcolorisblk this may sound lame, but the best way to pull off that jacket is to not be so insecure. Just wear your clothes and get comfortable wearing them. And as for the other stuff... how much time would spend listening to jerks in real life?
Not to keep harping on the poor city (especially as most people don't care), but I think this says a lot: http://www.cbc.ca/news/canada/ottawa/andrew-king-sparks-street-shirts-1.3537684I lived there for four years while going to school. After the initial novelty wore off, the best thing about it was its proximity to Montreal.But I'm sure D.C. is a lovely city. I look forward to visiting it at some point.
Take a photo elsewhere in your house, and either use a timer or get someone else to take it. The fit looks fine, except the ripped jeans with box-fresh white sneakers looks incongruous. And the way you've got the jeans tucked beneath the tongues of your shoes makes the jeans look too skinny, or the shoes too big, or both.