I came here to post something at the OP like "wow you cracked the code, his personal brand is becoming obvious and less cool." But this guy actually hit the nail on the head and made a much better point.
It's all trends; everything is trends. Seeing past them means actively trying to look past them.
ALTHOUGH, as an old late-20's fart, I WILL ADMIT, I stopped a college recently, and the number of frat dudes in slimline khaki baseball caps and oversized plaid shirts was fucking stupid. Like a uniform.