You look like a total square in almost all your pictures. I dont mean that in a bad way at all, I mean you look like a somewhat conservative and successful white collar person of some type. Probably refined and averse to obnoxious music and grungy scenes. I guess this is based on your pose, hair, expression and backgrounds. With that baseline, any sort of "edgy youthful"outfit just looks really silly to me.
A look like this one here looks great. Stylish in an adult sort of way and nicely balanced.
Appropriate amount of slut in the shirt also. Well done.
And Hendrix, shit man, that orange looks heinous in that color mix. You say it's spring over there?
Oh and I would like to echo that the shorts/leggings combo looks great on Brad. Not sold on the top half but not a deal killer either way. Nice concrete jungle safari vibe.