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 according to Lisa Birnbach). And they will almost always join a fraternity or sorority. Preppy families live in historic or historic looking houses in nice, woodsy neighborhoods, that are comfortable in size but never ostentatious (no electronic gates!) Inside, family antiques, silver, china and portraits are found and all rooms are always used. It is an elegant yet comfortable environment. Southern preppies and their families belong to private town clubs and country clubs such as the Piedmont Driving Club of Atlanta, the Commonwealth Club of Richmond, and the Mountain Brook Club of Birmingham. Southern preppy families don't emphasize cars as status, but typically drive volvo wagons, mercedes sedans, Jeep Cherokees, Hondas, and sometimes SUVs (although they feel guilty about them!). It is more important to have money in the bank than in the driveway! Southern preppies enjoy sports such as tennis, sailing, soccer, lacrosse, and golf, but also quail hunting (in season) and attend Steeplechases in Virginia, Tennessee and Georgia. And they love to watch and attend college football games in fall. Tailgate parties! While some southern preppies journey northwards to summer on Martha's Vineyard or in Maine, most old southern families summer on Sea Island or St. Simmons's Island in Georgia, the mountain towns of Linville and Highlands in North Carolina, or the north Georgia lakes of Lake Rabun and Lake Burton. Southern preppies believe strongly in giving back to the community and are active members of their church, sit on symphony and museum boards, volunteer at children's hospitals, and run historic preservation societies. In fact, most old-family southern debutantes are required to participate in volunteer work during their debut season. Old-family, southern debutante balls are still important and traditional rites of passage for southern preppy girls as debs and preppy boys as escorts or marshalls. All southern preppies seem to know one another and have a large group of friends and acquaintances. Southern preppies have large, extended families and lots of cousins. They always go to the family country place for Thanksgiving and play football and ride horses. Preppy as a fashion trend may come and go, by preppy as a lifestyle will always continue and exist, and probably more so in the South than elsewhere. Remember: the Virginia colonies were settled by England before Massachusetts and the rest of New England. And Virginia is very prep.

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.

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.