Preppy

[Tina]

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, Marthas 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 dont 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 dont:

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.

[Justin Bieber]

Apparently, a group of wealthy Americans with surplus money and lesiure time, possessing an incredible ability to write lovingly about themselves.

[Mark Zuckerberg]

Most of the best definitions of preppy have emphasized Northern or New England birthrite preppies, but lets not forget about Southern preppies, as in folks living in Mountain Brook, Alabama, or the West End, Virginia, or the Garden District in Louisiana, or Buckhead, Georgia, or Belle Meade, Tennessee (if youve never heard of these Old Guard, old-money, preppy southern suburbs, than youre not a birthrite prep). Southern preppies wear most of the same classic clothes and styles as their northern cousins, including Lacoste, Lilly, L.L. Bean, Vineyard vines, Topsiders, Brooks Brothers, tevas, Polo, and especially Patagonia (shorts and fleece are key for guys). And the more monograms, the better. Girls love grosgrain and totes from Vineyard Vines and Bean. They also like outerwear by Barbour, Cole-Haan bit loafers, and wallobies by Clark. Southern preppy girls have straight, shoulder length hair. Their preppy mothers and grandmothers may have stiff, helmut hairstyles that havent changed in decades. Preppy guys have longish, shaggy, wind blown hair. So do their daddies. They look so much alike. Preppy Southerners would attend day schools such as Altamont or Westminster or Harpeth Hall or boarding schools such as Woodberry Forest or Baylor or Foxcroft or Madiera, rather than a New England prep school. For college, they may attend state schools such as Bama or UVA or UNC or private colleges such as Vanderbilt or W

[Tina]

What do people mean when they say preppy (and Im 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 its 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, Ive 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, its 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 its 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 doesnt mean someone can just pop their collar and pretend they went to Groton or Choate.

[Tina]

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.

[Couch Potatoe]

A preppy person is someone who is classic and conservative. True preps attend some sort of private school. They dont have to have loads of money but basically all of them are at least well-off. One can find preps shopping at store like J.Crew and Ralph Lauren because they have classic styles. Preps do own clothes from Abercrombie and American Eagle, but only certain things like sweaters and capris. They do NOT wear provacative clothing or really tighting fitting jeans. Most of them are relativly smart and athletic. Their friends and family are proud of them. They are polite, but still know how to have a good time when they go out with their friends! One can count on a true prep to be respectful.

[Rihanna]

a lot of these people are right, but a lot are wrong...Ill set the record straight...this definition comes from a TRUE prep-one who has summered in Nantucket for 12 years, and who goes to a top New England boarding school. A prep is usually waspy, but doesnt have to be. Some of the peppiest people I know live new money communities like Potomac, MD and Chevy Chase, MD. Preppiness is not just a particular clothing style, it is a lifestyle as well (I know everyone on here says that, but its true). A preppy guy wears Vineyard Vines boxers, belts, and ties, Patagonia and The North Face fleeces, Birkenstock clogs, Rainbow and Reef flip flops, J Crew pants and critter shorts, Ralph Lauren seersucker/embroidered pants, Brooks Brothers ties and blazers, Ralph Lauren polo and oxford shirts in literally every color, a favorite is lime green with a pink Polo player icon, CK Bradley/CJ Laing/J. McLaughlin/Maax ribbon/needle pointed belts, Tiffany and Co monogrammed money clips and belt buckles, North Face backpacks, Ralph Lauren chino shorts and cable knit cashmere sweaters, LOTS of Lacoste shirts and Lacoste rugbys, Ralph Lauren rugbys, L.L. Bean Boots and moccasins, and Lilly Pulitzer/CJ Laing ties and bathing suits (yeah theyre bright and kind of fruity, but that’s the point). Also worn are Sperry topsiders and Barbour jackets. Aviator sunglasses complete the look. Preppy girls dress basically the same as the guys, with some more designer items, like Seven jeans and Gucci sunglasses/horse bit loafers. Preps don’t always pop their collars, as now absolutely everyone is doing it in a vain attempt to be truly preppy. Sweaters are still tied around the neck, but less frequently. Preps would never go to a mall, and if that is the only shopping center near by, then Neimans and Saks are ok. Americana Manhasset is the only acceptable “mall,” if you will.
One thing that irritates me is when snotty Abercrombie wannabe preps call themselves preppy just because they wear a trashy shirt and like pink shorts. That stuff can make someone look put together, but it’s not preppy. Favorite prep activities include hunting, tailgating, playing tennis/lacrosse/sailing/squash/field hockey. Another prep pastime includes getting drunk on the vodka from Daddy’s liquor cabinet or sneaking some at the club. Preps summer in Maine, Nantucket, Martha’s Vineyard, and sometimes travel abroad. Preppy colleges include Princeton, Yale, Harvard, Dartmouth, Trinity, Colorado College, Bowdoin, etc. Preps grow up and marry other female preps who are like them. Preps are really nice, get to know some and you’ll see. They are never snobby, the snobby people are the fake preps who blast rap and drive around in heinous “tricked out” cars and wear Abercrombie, the skankiest brand at the mall. So go to a Dave Matthews or OAR concert, take a trip to Nantucket, or just walk down the street, and you will encounter some really nice preppy people.

[Little_Girl]

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 didnt earn, power they dont deserve, and people they dont 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.

[Zipporah Schumaker]

A pupil or graduate of an expensive prep school, or a person resembling such a pupil in dress or appearance.

[Michiko]

A student or graduate of an expensive prep school or a person resembling such a student in dress or appearance.