Have you ever thought of going with the mystery-bad-boy style? Leather jacket biker boots etc? Just don't try to go gangster, that would look weird. Or you could go with a checkered shirt (casual) and jeans with sneakers. Or you could color co-ordinate, you look around for colors for clothes that match your complexion and the area you want focused on, just don't wear anything too slimming or that's too big for your body. Slimming would classify you as skaterboy, and big shirts might classify you as wanna-be-gangster.
hipster-ish except less annoying. fitted shirts that bring out your masculinity I guess. I don't know you look like you can pretty much wear anything but avoid preppy logos/companies cause you'd look better dressing mature.
based on your looks, I would think stuff like these would look good on you: