Take it from Adam Gallagher, Lookbook star from Riverside, California how to simultaneously dress down a preppy tie and a camel coat while spiffy-fying a casual button-down and tee. Yes matching (tie and socks) have something to do with it as good fit (chinos).
Here: tie, hair, and bag. Though the hair has a lot to do with it, I think it is mostly about taking things out of their context: partially removing the dandy out of this plaid blazer (and the previous coat) and tying it together (literally, with a knot) with the disheveled pose of the pseudo-intellectual university freshman.