Warning: Spoiler! (Click to show)
I know this is going to sound insulting, but you look like a paperboy from the 1940's. That's a pretty fucking cool look to be able to pull off.
It's nothing super-amazing in terms of quality, but I got it for a great price, it fits amazing (if you're small-medium go for small), and it keeps warmth in and rain out (if closed) very well.
It's a bit..."shiny" (dunno how else to put it), my sister doesn't like it, I don't mind it, but you should still know about it before buying
Well unfortunately that blazer and those nikes are the only real cool items in his wardrobe, but he has some other rather nice stuff too
don't worry, if he puts on a good fit i'll post it
It's this one
And yeah, I agree about what you said about posting a bunch all in one post, so edited it a bit