regarding the pinroll, I hardly ever see the point. Berlin´s outfit looks great, and a pinroll would make it less classic and more try-hard, which isnt really a good thing. personally I like a wider straight leg rolled up..
great outfit! I really think that works for you, with the tucked shirt and somewhat loose pants, and i think its because you got rather short legs! the proportions look good imo. badass!
some boots might push it over the edge to aswsome...