Preppy. Tricky little word. I think im gonna start with dictionary.com's definition:

A student or former student of a preparatory school.
A person whose manner and dress are deemed typical of traditional preparatory schools.

Obviously the definition that is more commonly thought of is the 2nd one. (even tho its a noun. nowadays, "preppy" is thought more of an adjective, rather than a noun. more of that will be explained later) However, when someone thinks of "preppy" nowadays, they think differently. the "prep look" (in the olden days) consisted of a suit, smartly done hair, and expensive shoes. (only rich people could send their kids to prep schools) these "prepies" no doubt behaved and dressed in a different maner than kids who had regular educations. when the word "preps", "preppy", "preppies" etc, started to be introduced into mainstream america, the meaning somehow changed from the traditional meaning, just as other things change, to the meaning today. "preps" started to be a word for people who dressed and acted a certain way (much like the old preppies). preps act "preppy". nowadays, the prime sign of a "prep" for a girl is someone who wears polos (always with the collar popped up), skirts (sometimes mini), or light-colored pants with a white ribbon belt or something similar, comfortable shoes (like tennis shoes), pearls, ponytails most often with a ribbon, or hair blow dried straight, and usually no makeup. their nails are kept nice, sometimes manicured with french tips or in a light cheerful color. black is almost non-existant in their wardrobe. conversly, pink and green are the main colors in their wardrobe, followed by white, blue, and red. same goes with men. however, some people do differ on some of these "signs of a prep". (example, a prep may wear a lot of makeup, or wear uncomfortable shoes) for boys, the polo is his only style of shirt (again, of course, with the collar popped), his pants always consists of cargos/khakis, and he wears loafers/comfortable shoes. their hair is short and neat (most of the time. there are, like the girls, variations on what "preppy" is). common clothing brands/stores preps are sure to wear are: ABERCROMBIE (a BIG one), charlotte russe, express, h&m, locoste, and tommy hilfiger, just to name a few. all clothes are worn in a "fitted" manor. (the girls wear tighter clothes than the boys tho) they all act in a snobbish manner. they exclude people who are not in their "exclusive" group. smartness, however varies from person to person. (usually, the preps in the olden days were smart b/c they went to actual prep schools.) however, the preps these days can be found in any (im gussing all) public schools, starting from, even, elementary schools. as the grades get higher, the preps get more and more noticeable. they also get meaner and meaner. preps (like their old counterparts) are reasonably rich (though maybe not that rich; but they certainly are NOT poor). preps are usually good to fairly good-looking. as always there are exceptions. i am not trying to be racicist, but they are usually caucasion. on some occations, there are blacks and asians. and on very rare occasions, hispanics. (that was meant to be a joke. please dont take that very seriously-about the hispanics part) preps also tend to have blonde hair and blue eyes. they must always travel around in packs, especially the girls. if there is a group of less than 3 (at the very least) they consider that "uncool". and when they do travel around in packs, they must be very loud and giggly and take up 3/4 to all of the hall space, forbiding anyone trying to get through them. teasing or taunting people not in their group is a normalcy. usually, they pick on "geeky", "dorky", "neerdy", "socially inept", etc peers. the girls use words that are so razor sharp that they actually might cause another girl to kill herself. the girls only talk about gossip. the boys are more physical, especially in the gym locker rooms. they might use their towels to snap them at other students, but that is not the furthest they will go to physically torment their peers. they usually come from excellent families, whose parents love them and parents that actually acted the same way like them in high school. preps' parents tend to have a blind eye towards their activities. preps go to the mall every week (at least) and watch tv shows such as The O.C, TRL, etc. most often they are in relationships with members of the opposite sex within their groups (sometimes refered to as "cliques"), and lose their virginities prior to graduating high school. Sometimes the girls talk a certain way that can annoy the hell out of you. (ex. "oh. my. god. she said that?? omg. i am like, so pissed now, like, i could kill her, like, u know, i hate her! like, she shouldnt have said that, like, who does she think she is??? its almost if shes like, prejudice or something, like, like i dunno, like,like, rasist." --in respose to a girl who said "better pull up those gucci pants") preps tend to use "like" in their everyday sentences as if it were the word "the" or "I". the point is, they use "like" a LOT. the hc king and queen, the prom king and queen, the class and school presidents, anything that involves student body elections, a prep will always be them (as student body elections are always a popularity contest). the reason they win is b/c anyone excluded from their group are always wanting to be accepted. the teachers love the preps. one surefire way of telling who a prep is, is if they do school sports, and more immportantly which sport they take. for girls... CHEERLEADING. its a good excuse to wear short skirts and wave pom poms. (we all know what those pom poms mean! jkjk...) they wear ribbons in their hair and do the splits. its the all american sport. almost all cheerleaders are preps. tennis is also a VERY preppy sport. laccross may be preppy for girls, but as the sports get dirtier, they get less preppier. for boys, LACCROSS is the prime sport. since boys will be boys, getting a little dirty is ok. tennis is also a preppy sport for male preps. football may be played by male preps. the preps will give their letter jackets to their girlfriends to wear as well. a prep's mentality is, high school will last forever, therefore, they think only about having fun and becoming prom queen, or being voted, "most popular". i could go on and on about what makes a prep and prep, but that would take a very long time. however, i would like to leave with this note: all in all, when all is said and done, its the person's attitude that makes him/her a 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.

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.