Looking preppy isn't about popping your collar. I know lots of guys out there go for that whole "preppy, just walked out of Yale, old money" look. Sorry to inform you, but popping the collar ain't the way to do it - it doesn't make you look rich or cool. It is, in fact, the international symbol for douchiness, just like crossing your hands around your neck is the universal sign for choking.
Furthermore, the more collars you pop at once (see photo above) only exponentially increases the degree of douchiness and must be avoided at all costs. Instead, relax those collars boys. Let them rest neatly and casually against your neck. Don't layer your polos - one per day is plenty.
Just for reference, the only time you should ever wear a popped collar is when you are in this commercial.
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