adjective
This word found its start with the term "Prep School", or preperatory school, which is an elite high school where teenagers live in dormitories on campus. (i.e. Phillips Academy in Andover, Massachusetts - shout out to all my girls at PA!!!) Since these schools are populated by a particular class of people, with a particular style, the adjective PREPPY emerged.
'Preppy' can refer to members of a certain social class, but can also be more generally used as description of personal style.
In terms of style, the stereotype is a mixture of pink-and-green. Pants are typically khakis, Nantucket Reds, and, for men, often khaki-cotton-material in bright neon colors such as pink and lime green. The epitome of preppy pants are the latter, decorated by a pattern of sewn-in whales of a darker contrasting shade. Classic button-down shirts, usually solid or striped, are common, as well as solid and striped polos. The collars of the polo shirts are always "popped", or turned up instead of folded over. Often, polos of different colors are layered, the one on the bottom matching the skirt/pants, the belt, or the headband. Flip-flops are the coup de grace, no matter what the weather. However, when our toes are absolutely freezing off, we wear Uggs, with the tops folded over to expose the fur and our jeans tucked in. We wear v-neck cable-knits and argyles over button-downs. North Face jackets are a must. Pearls are best for jewelry. Excess hair products, jewelry, and make-up is frowned upon. Accessories include Nalgene bottles and tote bags.
In terms of the lifestyle, "preps", or preppy people, typically live in the New England area. They usually belong to Yacht Clubs, Beach Clubs, or Country Clubs, depending on which crowd they run with (i.e. The Eastern Yacht Club in Marblehead, Massachusetts). Their children go to private elementary and middle schools, and are attended by foreign female au pairs, to keep them out of their parents' way until they can be shipped off to boarding school (not that we mind much). They dress in preppy clothes (see above), and spend much of their time shopping to find them. The Jewish kids among them throw fabulous bar mitzvahs during middle school, and if the WASPs and Catholic kids get jealous, we throw even more fabulous Sweet Sixteens, which are similar to bar mitzvahs escept with less religion and more liquor. We all know each other. All of us. I know, it's hard to believe, but somehow we are all intermarried, or at least have some mutual friends. The women are either housewives on committees and boards and things, or they are incredibly successful professionals, like partners in a law firm or the head neurosurgeon at a hospital. The fathers make lots of money, and are always gone on business, and play lots of golf. Acceptable sports are lacrosse, soccer, crew, polo, and sometimes water polo. We are either radically liberal (like my family) or radically conservative, but we don't discuss politics unless everyone in the room is on the same side. We will all get into an Ivy League school. This is a necessity. We summer on the Cape, or the Hamptons, or Nantucket. We spend March break in Atlantis and Cancun and other trendy resorts. Contrary to popular belief, not all preppy people are wealthy - but the more money you have, the easier it is to fulfill the lifestyle and to enjoy its benefits.

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. ...

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

Most of the best definitions of preppy have emphasized Northern or New England birthrite preppies, but let's 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 you've never heard of these Old Guard, old-money, preppy southern suburbs, than you're 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 haven't 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&L or Hamden-Sydney (the preppiest school in the country accord...

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" 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. ...

A preppy person is someone who is classic and conservative. True preps attend some sort of private school. They don't 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.

A prep is typically a well-educated, good-looking person who comes from a solid, well-established, "old-money" family. Preps lean towards conservatism, and generally are well-dressed and buttoned-down in public. A prep is inclined to wear clothes from Brooks, Lacoste, J. Crew, and Lily Pulitzer - NOT Abercrombie or American Eagle, as some non-preps believe. A prep is usually an all around good guy (or girl) and would be unlikely to brag about their status or wealth. Preps shouldn't be characterized as spoiled underachievers - if they were, where would top-tier schools like Princeton get their preppy reputations? Colleges and universites are becoming more democratic each year; an unqualified student wouldn't gain admittance on family wealth alone. People who bash preps have probably only had contact with the A & F, A & E kind of wannabe-prep - and in many cases I would agree with their comments. But a true prep is far more understated; they would drive a Volkswagen GTI over a Cadillac, vacation on the Vineyard or on Bermuda rather than on St. Bart's, favor subtlety over ostentation. The people on this site who don't like preps are either jealous or haven't actually met a real one.