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What do people mean when they say "preppy" (and [I'm not talking] about the slutty Abercrombie-type prep that everyone seems to talk about here).....?

Preppy as in boarding schools and summers on nantucket. Preppy as in WASP and old money. As in LL Bean fur moccasins and ribbons in your hair, and flip-flops when it's 10 degrees outside. As in sailing and Topsiders and looking back on your house from your boat and being so, so happy. Preppy as in buying clothes not for the label but for what they look like. Preppy as in collars [up and] Nantucket Red shorts faded to pink. As in crew, tennis, squash, lacrosse. As in [Connecticut], [Massachusetts], [New Hampshire], Maine. As in Ivy League and prep schools with the word "academy" in their names.

As you can probably tell, I've had a lot of experience with this sort of person...and I suppose I am one...but so what if I summer on the Cape and wear blue seersucker and play tennis? Preppy is not a trend, it's a LIFESTYLE...it can never go out of fashion. There will always be people trying to emulate the preppy clothes and thinking they are preps, but really it's about your background and your education and where you summer. Not everyone who wears Lilly is a prep-- there is certain fashion that preppies usually wear, but that doesn't mean someone can just pop their collar and pretend they went to Groton or Choate.

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