I know youv heard it before but it is extremely true: preppy is not about what u wear it is about the lifestyle. Most preps are born preppy into a preppy family. the most preppy is “waspy” families (white anglo-saxon protestant), followed behind by catholics and jews, although i have seen many black, hispanic, asian etc preps too.
-PREPPY CLOTHING: Preppy stores are mainly the ones you can find in nordstrom or bloomingdales: lacoste, ralph lauren, and many others. North Faces are the newest jackets for preps, and abercrombie could be considered the "neo-prep" by some, but dont overbuy abercrombie. Hollister and Aeropostale is not preppy, but preps can own clothes from there. American Eagle can be preppy, but as abercrombie dont overbuy. For males, polos are a must, in many colors. Khakis, rope belts and bracelets, sandals, sweaters or north face fleeces, etc. Girls have a larger variety, included polos as well, tanks, khakis, fitting sweaters, ribbons, rope belts, sandals etc ( beleive me there are a LOT more)
-PREPPY AREAS: Most preps live in the northeast, but many can be found in California. Westchester, NY; Greenwich, CT, etc are places where many preps can be found. Most attend prep or boarding schools, yet many attend suburban public schools. They do well in school, which runs in their family, and go off to similar colleges as their parents, primarily ivy league
-PREPPY CARS: Preppy cars are important for they are the first impression in many cases. Preppy families should have at least three cars: An SUV, a sedan, and a sports car. Mercedes, BMW, Lexus ect make great SUVs and sedans, as well as sports cars. But for sports cars, its necessary to think out of the box. Porsches are popular for preps
-PREPPY ATTITUDE AND OVERALL LIFESTYLE: Preps have many friends but may not be the most popular in their school. They are not stuck up and find no need to brag, people already know they are rich. Prep dads are business executives and real estate investors. Mothers are usually working mothers, either involved in their husbands business or successful on their own (for example successful lawyers). They are NOT stuck up, as their children, but they enjoy to spend time with families similar to theirs. They are not unaware of their children's lives, yet they dont need to be too involved because their children are doing fine on their own.
-PREPPY SPORTS AND ACTIVITES: Preps play sports they can play their entire lives, tennis and golf at their country clubs with their family and family friends, as well as lacrosse or soccer at their schools. Girls can be cheerleaders, but its not necessary
-PREPPY PETS: Preps do NOT have small ugly dogs that they carry around with them. Usually preps hav medium sized white dogs (such as bichons or poodles) or large, dark furred dogs with their heads high (such as Great Danes).
-PREPPY HOMES: Preps live in large houses, with European style exteriors and neo-classic, antique interiors. They also have other houses, such as winter homes in the mountains or summer homes. Florida condos are a popular vacation spots for preps. Winter is spent skiing, in Colorado and the Alps; Spring break is spent in the Hamptons, or Florida, or other vacation spots. Summer is spent in Europe and at the country club. Family trips dominate parent trips (usually to vineyards) but they are popular too.
Overall, preps are the ideal person, in the ideal family and the ideal school. They are moderately rich, and will be rich when they grow up. Many have "old money", but still some dont. They have an attitude that is NOT stuck up, yet still hav an air of importance. Preppy Brand names, country clubs, and trips to preppy vacation spots are important. And ultimately bragging is unnecessary, if you really are preppy and rich, people will know.

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.