<p>I attend Choate Rosemary Hall. I live in Greenwich, CT. I wear vineyard vines pants, button downs, and belts; Ralph Lauren Polos and sweaters, Sperry Docksiders, and Brooks Brothers Suits. I summer on Nantucket as well as international travel. People from the Midwest are not preppy. You must be from New England and attend a New England Boarding school like Choate, Hotchkiss, Taft, Andover, Exeter, St. Pauls, Groton, or Deerfield. You do not need to be from old money but you must be well off financially.</p>
<p>I agree with jhall14 in regards to being a “true prep”, however I will add that you can find authentic looking preps in the Midwest, who adhere to the “true prep” clothing guidelines, who vacation in Maine and Vermont, and who are gearing up for an Ivy League college if not a top 20 U.S. college. The only difference is that they do not live in New England. </p>
<p>As far as the fashion, A&F, Hollister, American Eagle, et. al. are not preppy lines of clothes. The whole prep style, outside of a crested blazer, is based all about comfort and being casual. A blazer itself is a casual item. Tennis clothing, yachting gear, polo shirts, shirts with button-down collars, chinos, boating shoes, moccasins, etc. are all casual (usually sporting) wear to the wealthy in the same way that a plain t-shirt and blue jeans are casual wear for the middle class. The clothing is more indicative of a leisurely life-style combined with a bit of rebelling (such as popping your collar or wearing a foul weather jacket aka a yachting or boating jacket over your blazer). </p>
<p>The whole point is to look like you just came from the yacht club, or you are on your way to it.</p>
<p>Lol, A&F is labeled as ‘casual luxury’. I have never seen A&F sell another type of shoes besides flip flops and sandals. </p>
<p>I think preppy is along the lines of a polo tee shirt, a white tennis skirt, and some non-sandals LOL.</p>