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There are the private old school, polo shirt & loafer wearing preppies that summer in Nantucket and love sailing, rugby, squash, etc. Then there are the public school, mall shopping, Abercrombie and Finch wearing preppies who love football. You can even hear the difference in their grammar (Old school don't use valley girl as do public school) and speech. For instance when a person says apple, car and please. Old school would say "for instance", Public school says "like".

They are two different groups. Public school preps (PSP) have a tendency to "need" to point out to others they are popular while in high school. Where an old school prep (OSP) is concerned with family pride and life style that lasts into adulthood and until they die. True the OSP made say something not nice BUT they are polite most of the time. PSP often are rude to others. Want to get back at a PSP? Tell them they are not OPS which is what they are imitating whether they realize it or not. When they say they are, ask them when their family arrive in America was it over 200 years ago? Or when the last time they went sailing?

Preppy is slang for preparatory school. A pubic high school, though provides a good education, is not prep-school where students take college level classes. There should be two different names for old school prep (OSP) and public school prep (PSP).
OSP Girl: "Daniel, a PSP is waving at you." PSP Girl says to Nathanial: "Oh, My, God ! Dan, I have not seen you in sooooo long." Grabs at Daniel for a hug. Daniel unhappy but polite: "Hi, ah...Niki. What are you doing here?" "I can't believe I ran into you...OMG It is totally awesome to see you...Do you like my preppy new shoes?" OSP Girl: "Hello, I am sorry to interrupt your conversation but we are on our way to meet some of our friends. It was a pleasure meeting you." PSP: OMG it was totally awesome to run into you. We should get together. Wait let me send you a text."
by We Have Been Here March 10, 2010
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A true preppy is someone who:
Wears, but is not limited to, Polo, Lilly, Brooks Brothers, Lacoste, LL Bean (ie duck boots), ribbon belts, prints (ie cords with embroidered whales, palm trees, etc), sweaters tied around the neck, collar always popped, looks neat and put together. Hair ribbons or ribbon headbands, pearls, and other classic jewelry pull the look together. Preppies are partial to monogrammed and engraved items (ie tote bags, oxford shirts, jewelry, money clips, etc). Colors are always brite (favorites include pink and lime green). Preppies may not always match EXACTLY but they are always coordinated. Hats are worn (ie polo player, Lacoste, Brooks Brothers), but they are unique- not designs you would see in the mainstream and the "mall".
Preppies often attend prep schools (ie Middlesex School, Governor Dummer Academy, and Belmont Hill) followed by New England private colleges.
They are confident and unafraid to express their own styles and be daring in their fashions. Preppies vacation on Nantucket, Martha's Vineyard, Delray Beach, and on the coast of Maine. These vacation locales are places their families have been going to for years, and have histories there.
It is a common misconception that preppies are snobs. Many people view them as unapproachable, and as a result mislabel them. Preppies are not as rich as people may think they are, but they are often well off. They buy into classics rather than trends, and don't change their lifestyles with fads.
Preppies tend to have bizarre connections with other preppies they meet, always finding mutual friends/ family and people that run in the same circle.

Preppies don't:
* Wear tight, skin exposing clothing (ie fitted Abercrombie sexual tshirts with tight flared jeans)
* Limit themselves to mall shopping and chain stores. They gravitate towards long-established classic stores and boutiques unique to quaint New England towns.
* Wear heavy makeup and endless hair products. The phrase "less is more" is a preppy creed.
* Glue purses to their arms, especially when going to school. Lip gloss and if need be, a wallet, are thrown into tote bags along with books.
Les whispered to Tyler that Linds looked very preppy with her pink popped Pulitzer, cable knit cardigan and pearls.
by sayler December 28, 2003
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Preppies are people who go to prepatory highschools (Groton, Hotchkiss, Philips Exeter, Philips Andover, Deerfield, Laurence, etc.). Most of them shop at J. Crew, Banana Republic, Brooks Brothers, L.L. Bean, Ralph Lauren and all designer stores. Preppies are often mistaken for kids who shop at Abercrombie & Fitch, American Eagle Outfiters, Rave, etc. Those who think "preppies" are girls who shop at those stores are VERY wrong.
You could tell by the way they were clad in Brooks Brothers that they were utter preppies.
by BcBK March 16, 2006
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Apparently, a group of wealthy Americans with surplus money and lesiure time, possessing an incredible ability to write lovingly about themselves.
Every other definition on this page.
by scose January 13, 2005
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As a public school teacher, I can speak to this topic with some authority. The term "preppy" originally described members of old-money patrician families with traditional ties to private bording schools. They live on the East Coast or in the South, and they can afford to "summer" places.

At their best, true preps preserve the best traditions of Western Civilization. They try to be honest, humble, brave, principled and public-spirited. They wear simple, elegant, well-made clothing, and they wear it until it falls apart. The manufacturer is unimportant; true preps respect good craftsmanship, not expensive pricing. Although they wear the Classic American Wardrobe, they realize that they did not invent it (except for boat shoes... your grandfathers DID invent boat shoes), and they have no exclusive claim to it.


Classic preps with noteworthy ancestors see their forebears as people to be lived up to, rather than people to be bragged about. They recognize their privileged status, and they work to become worthy of it.

Classic preps work hard to develop both mind and body; achievement in both the classroom and on the athletic field are highly valued.

At their worst, preps are snobs. They take pride in money they didn't earn, power they don't deserve, and people they don't value. When they die they leave behind them an ocean of gin and tonic, a garage full of fine automobiles, a fantastic wardrobe, and a wasted life. It is good to appear in their will, but bad to appear in their presence.

Nowadays, though, the term commonly describes the upper strata of "popular" kids in many American highschools. I would argue that since this group vastly outnumbers traditional preppies, they perhaps have staked a greater claim to the word.
See that kid with the black pants, the nose ring and the mohawk? Instead of shoving him into a locker, I think I'll introduce myself and shake his hand, because I'm a true preppy.
by David Medlock August 22, 2005
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n., as used in Love Story (written by Erich Segal, made in the early '70s)-- a "preppy"/"preppie" is one who is preppy.

adj., old money, classy, conservative, tasteful. See several definitions above: private schools and first-class colleges or legacies at colleges. Philanthropy is also valued. As far as clothing goes, these days it's mainly Polo, Burberry, Lacoste, Brooks Bros., L.L. Bean, etc. Preppiness is usually found on the East Coast, most often... it seems that several people are limiting it to New England, which is not right. I have enough friends from Richmond and Raleigh and New Orleans and Atlanta to tell you that preppiness is alive and well in the South-- it's often almost exaggerated down here.
n.-- Charlotte grew up a preppy, shunning her family's new-money, money-wasting ways.

adj.-- Hunt looked rather preppy in his duck boots sans socks and his Nantucket Reds shorts.
by MFer August 03, 2004
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Preppy can refer to a conservative, timeless style of dress and the simple choices of classic jewelry that evoke an air of confidence in one's natural beauty. But a true preppy attends a Boarding School. Their parent or parents often attended traditional boarding academies such as Phillips Exeter, Phillips Andover, Deerfield, Hotchkiss, St.Paul's, Groton, St.George's, Choate-Rosemary Hall, Lawrenceville and the like. They grew up knowing this was their likely educational path and never thought it was odd to leave home for High School. They hope to attend an Ivy, Stanford, Cal or one of the monied Northeast private colleges such as Middlebury, Williams, Trinity or Bowdoin etc.
They may have grown up in California but they likely have east coast family ties and live a pretty bicoastal existence once they start "Prep School". They usually play lots of sports and know where the squash courts are as well as what a "shell" is or they are a really accomplished musician. They look out their dorm window and see brick or Gothic stone; as well as Patagonia and North Face clad preps sometimes playing with little "fac brats" on the expansive grassy lawns. They often learn at oval tables rather than at traditional classroom desks. They are often sleep deprived because of the demands of 24/7 dorm-life, sports, clubs and study. They sometimes have to fake sick and go to the Infirmary since that is the only way to skip class and sleep without getting into trouble with warnings like "green cards" or "dickies". They sometimes get "put up" for discipline issues that would just involve being grounded if they lived at home. They sometimes get stressed and burned out and move back home. It's possible to be forced to withdraw from the academy. They often graduate with really tight lifelong friendships and are so loyal to their Alma Mater that when they die they leave generous endowments from their estate to their "Prep School" and hope their grandchildren will attend as legacies and enjoy the benefits of their alumni giving.
by JGS August 28, 2005
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