I don't know why, but red plaid flannel just goes so excellently with dark denim, and so even if this is very lumberjack-y I just can't resist pairing them together. But so I don't look exactly like I'm off to fell timber, I added some sassy acqua pumps (Nava) and a nice gold bib necklace (Punk Kikay). Let's see you cut trees in that!
Another trick -- the half-tuck. A full-tuck tends to look "proper male college student" to me while untucked is much too billowy. The half-tuck is just the right amount of laid back fasyon.