Dadcoring it up tonight. Yeah the whole pants boots situation is full-retard in this pic, i just stood up and my loop dealies so it looks wack. Also they're too close in colour. Yeah piss-poor fit overall. Deets:
They're an American thing not as a fashion item but as workwear, where it's a pretty old tradition - http://en.wikipedia.org/wiki/Levi_Strauss_%26_Co.
jacket looks a bit sloppy, maybe let a tailor take in the sides a little?
otherwise, just put on a button-down in some nice color (green/red/grey)
if you wanna go with a tee, you need a longer and slimmer one
You can barely see his tee. How do you know it should be slimmer?
I think he should just wear a dark grey/black scoop neck tee with some nicer sneakers or boots and the fit would be good, although very typical for SF.