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As a person who is rather familiar with the 'preppy' lifestyle I though I should clarify some of the definations in here.
A TRUE prep DOES NOT wear Abercrombie & Fitch, American Eagle, Hollister ect. nor do they wear slutty or revealing clothes.
They DO wear Lacoste, Ralph Lauren Polo, Lilly, Brooks Brothers, L.L. Bean, North Face, Birkinstock and J.Crew. Sweaters are worn around the neck and collars are always popped. Ribbons are often worn as belts and/or in their hair. Girls wear little or no makeup. They love pearls. For boys, nantucket red khakis are a must. Some wear layerd polos.
Most preppies attend private schools (ie Tabor Academy) and then private colleges in New England.
Many live in the New England area (Massachusetts, Connecticut sometimes New York) Most people sterotype them to be rich and stuck up but this is mostly not the case. Most preps do not flaunt their money.
Sports include sailing (a must), golf, tennis, lacrosse, soccer and skiing.
Many prep families vacation in Vermont in the winter and Cape Cod, Nantucket or Martha's Vineyard in the summer.
There are many 'wannabe' preps floating around today because they think it is 'cool.' Real preppies have been so since birth. They usually come form a long line of preps.
also see wasp
Elizabeth sighed, "They think they're 'cool' with their A&F polos and AE skirts." James agreed as he adjusted the sails on their sailboat.
by jessica December 29, 2005
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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.
"Preppy is a lifestyle, not a clothing style," Bitsy sighed as she observed the West Coast girls trying to pull off Reds. Her friend Buffy nodded before they resumed their tennis game.
by Lilly April 21, 2004
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Preppy is a lifestyle, not just a way of dressing. I am a southern prep myself, and this is how I would describe myself and my friends:

We're friendly, polite, and laid-back people. When it comes to fashion, we go for classics: polos, chinos, boat shoes, etc. We like Lacoste, Ralph Lauren, and J. Crew (a huge personal favorite of mine because of their extremely cute cardigans), but we can also shop at stores like Abercrombie and Fitch and American Eagle. However, when we shop at those places, we pass over the trendy, revealing clothing items and find our good old classics. Our closets are full of bright colors that we like and are easy to mix together. We don't wear makeup and our hair is simple, but pretty. We've been raised to enjoy the outdoors and sports such as tennis, golf, and lacrosse (mostly for the boys). True preps do not walk around with tights clothes and tons of mascara while ridiculing their peers; we preps are way above that, and instead like to try to reach out to everyone and never mind making new friends. A prep has a ready smile (not because we're brainless, but because we're kind and know how good a smile can make someone feel) and is always willing to discuss intelligent matters. (Keep in mind, there are exclusions to the rule. Yes, there are mean preps, and unintelligent preps, but on the whole, we are a good set of people.) True preps do not brag about tacky things like money. We don't feel the need to always have the absolute newest outfit (that's the whole idea of having a wardrobe filled with classics) and we don't over-accessorize, though we do like a simple string of pearls and a headband or ribbon. We wear our clothes for a very long time (until they wear out) and then we are very likely to replace them with something identical, or almost identical. We like to pop our collars, but we can also wear them folded and down. We are upper-middle class or upper class, but it's not a big deal.

Those of you that say preps are mean, slutty people have obviously never met a real prep, and I'm sorry that you have such a negative, skewed image of us. We're really just all-americans, after all.
Ellie smiled at her reflection quickly in the mirror, straightening her crisp, preppy, popped collar and her pretty argyle cardigan on her way out the door.
by Eleanor R. January 27, 2008
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"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.
(so yes, those of you who define preppy as:LOVES A+F, PINK, MAKEUP,MAKING FUN OF GOTHS and CHEERLEADING!!!!! are wrong)

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/topsiders, 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.
by _Kate_ February 16, 2004
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Preppies live very privileged lives (and we all know it too) and they are grateful for the opportunities given to them. They realize that not everyone lives a charmed life and are therefore not brats such as those on MTV's Super Sweet 16, but rather they acknowledge how much mom and dad have done to give them a good life, and are properly grateful.

Another defining characteristic of preppies is their work ethic. Preppies work hard for top grades and to be admitted to top-tier prep schools and colleges. The myth about daddy paying for lazy kids to go to Yale is not true. Our parents feel we should work to get to the top, and our work ethic usually pays off, which is why you find us at colleges such as Dartmouth and Yale.

There is, of course, the matter of the distinct preppy clothing style. Rather than the mall shops such as Hollister and American Eagle where the so-called "mainstream preps" shop, a real New England preppy shops at stores such as Vineyard Vines, J.Crew, Ralph Lauren, Lacoste, and Murray's. These clothes are admittedly more expensive than those found in the mall, but they are of much better quality, and therefore last longer, proving to be a smarter, better investment. The reason we can get away with wearing clothing for so long is because preppies do not follow trends. Our style of polos (collars popped essentially until marriage), khakis, topsiders, and other classic pieces has been in style for decades, and will continue to be in style for decades to come.
A preppy has been given opportunities but rather than waste them or take them for granted he or she works to earn this privilege after the fact. Class act.
by Nantucketreds0527 April 8, 2010
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Obviously there is much confusion on here as to what a prep is.... I suppose this is the kind of word that can be defined by where "someone sits" so to speak. However most of the definitions here are from kids in middle class towns who describe the "cool" crowd at their school. Sorry but a kid who wears Ambercrombie and drives a Civic is not a prep. It is a lifestyle. Even if you are very rich you still may not be a prep. Preps are mostly located in lower coastal CT. Parts of Mass., Southampton, and parts of Rhode Island. Most of the kids here have never seen a true prep. The clothes of choice are Brooks Brothers, J.Crew, Burberry, Lacoste and Lily Pultizer. They usually drive BMWS, Volvos, Jeeps or Benzs. They don't wear much make up.
The A&E clad jock in a middle class public school is not a prep. He is just popular

The kid driving a vintage car draped in Polo pulling up to his families equestrian country home is.
by A prep hater August 27, 2004
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Loves beach music - R&B from the 50s and 60s, dances the shag at the Carolina Grand Strand. Ladies wear colorful flats or sandals with leather soles. Summer capris with martini glasses or palm trees and matching sleeveless tops - not low cut. In winter might wear plaid culottes and Christmas tree ornament earrings. Will wear sequined tops with oceanic creatures on them. Guys wear khakis and loafers with no socks. Also very fond of sixties music.
Another summer look for ladies - sleeveless oxfords with belted khaki shorts and flip flops. Very enthusiastic, go to church and join the Junior League or other community service. Big on football and basketball and golf. Will also dance barefoot. 60s flower power also big with the ladies. Love kitchy pocketbooks. Ladies have very big smiles. The flip and the bob are popular hairstyles for ladies. Houses loaded with family antiques.
This preppy girl's favorite brands of the sixties were John Meyer, Ladybug, Villager and Papagallo. She loved the bold prints of Merimekko. And always Lily. She Carolina shagged to "Sixty Minute Man," "Under the Boardwalk," "Ms. Grace," "A Quiet Place," and "My Girl." She danced to the Tams in a former tobacco warehouse, especially "Be Young, Be Foolish, Be Happy."
by sandflea September 16, 2005
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