Double Pop

At first I didn't get the double pop. But I like to layer my shirts. If you're wearing two polos, what else are you supposed to do? And besides, if you are going for the ultra-preppy look (guilty as charged!) the double pop is the way to go.

Winter

Duffel coats are perfect for winter. Versatile and so preppy. I wear mine all the time: Work or play. Over a suit, sport coat or sweater. With wool trousers or levis. Hood up when cold!

Gay or Preppy

This article appeared in Details magazine a few years ago. The commentary (click to enlarge) is mildly amusing but I don't think there is anything funny about the way this guy is dressed. Looks normal to me. As for the question, gay or preppy, let's not forget those two labels are not mutually exclusive.