CPO Shirt Brown/Red/Khaki Windowpane Tweed

Talk about vintage-inspired — in 1971, it was like, don't even come to school if you don't have a CPO shirt. The idea is a little older than that, even (it's modeled after the jackets issued to chief petty officers at sea), but updated for a fully modern, more wearable look in a toothy windowpane tweed from Portugal. And speaking of wearable, there are a lot of ways to do it: layered with a chambray or oxford shirt, open over a shetland sweater, or underneath a heavier coat. Any way you do it, keep the fit easy and the hem untucked, and you're golden.