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<p>not necessarily. the definition of preppiness, after all, is “of, pertaining to, or characteristic of preparatory schools or their students” (<a href=“http://www.dictionary.com)%5B/url%5D”>www.dictionary.com)</a>, and yale has long had a greater percentage and greater number of preparatory school students than has princeton.</p>
<p>That’s not true at all. You can’t just go by the % of private school students, because many of those are actually from urban parochial schools that draw mostly disadvantaged students, and also because even at the “prep” or “boarding” schools themselves, many of the students these days are on financial aid and do not come from the typical background you would associate with such high schools. Your best bet if you want to see how “preppy” a place is is to visit for a few days, including a weekend evening and a weekday, and sample the social life for yourself.</p>
<p>Dictionary.com is a horrible, horrible dictionary quite frequently.</p>
<p>that being said here it does match the OED 
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<p>However it does have a more complex common usage, I think…</p>
<p>Here’s a definition of PREPPY from urban dictionary quite detailed, and much more interesting than dictionary.com’s</p>
<pre><code>“preppy” has come to mean the opposite or “punk” or “goth”-meaning unoriginal and stuck up, which is completely unfair to the true meaning of preppy.
</code></pre>
<p>the definition:
“preppy” is a lifestyle; that of many well-to-do and often “waspy” families of New England and New York; most preppy teenagers have been preppy since birth; have attended private/boarding schools in New England all of their lives; enjoy sophisticated, lifelong sports such as (but not restricted to)tennis, sailing, skiing, and golf. Many live in classically preppy areas such as New Canaan, CT; the North Shore, MA; Westchester County, NY; and Greenwich, CT. Many also have second or third homes in Vermont for skiing, or Nantucket/Block Island/Cape Cod for summers.
Many are legacies at boarding schools/colleges in the North East, many are talented but party as hard as they work; Most are old money (see wasp) but there are “nouveau riche” preps who may prefer more modern customs (ie. abercrombie etc) than the timeless classics of the “wasp” lifestyle.
Preppy clothing designers include (but are not limited to):
Lilly Pulitzer, Ralph Lauren, Petit Bateau, J.Crew, Anthropologie, Patagonia, Birkinstock, Brooks Brothers, Lacoste, C.K. Bradley, L.L. Bean, the North Face, etc.
Preppy Designers do NOT include:
Abercrombie and Fitch, Express, American Eagle, The Limited, Guess, Aeropostale, etc.
HOWEVER: preppy items may be found at many of these locations (ex: nantucket red girls chinos at American Eagle)
Preppy (girls) essentials include:
ribbon belts,minimal makeup (or better, none), minimal hair styling, pearls, oxfords, polos, chinos, birkinstock clogs, sauconys, headbands, cableknit sweaters, brightly colored pants, cropped pants, jack rogers sandals, lilly pulitzer sundresses, longchamp/herve chapelier/vineyard vines/ll bean totes, patagonia fleeces, reef sandals, JCrew bathing suits, rainbow sandals,moccasins/topside rs, and many more.
preppy (boys) essentials include:
brightly colored baseball hats, rainbow sandals, Ralph Lauren polo shirts (in ALL colors- the brighter the better), nautical rope bracelets, nantucket red khakis, messy/unkempt hair (or minimal styling), other brightly colored khakis/shorts, crewneck sweaters, flannel/plaid oxfords, rope belts, striped ties, vineyard vines ties, LL bean boots, patagonia fleeces, navy blazers + khakis, topsiders, and much more.</p>
<p>Read the Official Preppy Handbook.</p>