Preppy can refer to a conservative, timeless style of dress and the simple choices of classic jewelry that evoke an air of confidence in one's natural beauty. But a true preppy attends a Boarding School. Their parent or parents often attended traditional boarding academies such as Phillips Exeter, Phillips Andover, Deerfield, Hotchkiss, St.Paul's, Groton, St.George's, Choate-Rosemary Hall, Lawrenceville and the like. They grew up knowing this was their likely educational path and never thought it was odd to leave home for High School. They hope to attend an Ivy, Stanford, Cal or one of the monied Northeast private colleges such as Middlebury, Williams, Trinity or Bowdoin etc.
They may have grown up in California but they likely have east coast family ties and live a pretty bicoastal existence once they start "Prep School". They usually play lots of sports and know where the squash courts are as well as what a "shell" is or they are a really accomplished musician. They look out their dorm window and see brick or Gothic stone; as well as Patagonia and North Face clad preps sometimes playing with little "fac brats" on the expansive grassy lawns. They often learn at oval tables rather than at traditional classroom desks. They are often sleep deprived because of the demands of 24/7 dorm-life, sports, clubs and study. They sometimes have to fake sick and go to the Infirmary since that is the only way to skip class and sleep without getting into trouble with warnings like "green cards" or "dickies". They sometimes get "put up" for discipline issues that would just involve being grounded if they lived at home. They sometimes get stressed and burned out and move back home. It's possible to be forced to withdraw from the academy. They often graduate with really tight lifelong friendships and are so loyal to their Alma Mater that when they die they leave generous endowments from their estate to their "Prep School" and hope their grandchildren will attend as legacies and enjoy the benefits of their alumni giving.
by JGS August 28, 2005
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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.
Kappa Sigma at Hampden-Sydney is full of blond, shaggy hair guys who play lacrosse and are from Buckhead.
by Alex September 22, 2004
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Preppy is a dress style, a social culture and a way of life. Preppies have been around a long time. Their dress style and much of their way of life has changed only slightly since the 1950’s. While sometimes assumed to be rich, snobs, most preppies I know are very down to earth and nice.

My mother tells me that in the 1950s preppies were upper class kids who wore kilts, cashmere sweaters, madras plaid and Bass penny loafers. Name brands really were not the focus as much as quality. She attended private “prep” schools and attended debutante balls.

By the 1980s, when I was in college, the “Preppy Handbook” was published and preppy became all the rage and mainstream America embraced the look. True preppy kids still attended private schools, belonged to country clubs and enjoyed sports like sailing, golf, and lacrosse. The clothes that were in were more “matronly” than today’s preppy styles but certain brands became status symbols. Preps wore Polo shirts with the collar up (Izod Lacoste or Ralph Lauren), plaid wool kilts with knee socks and Bass penny loafers, Talbot’s, Lilly, Papagallo changeable purses, Pierre Deux purses, Nantucket reds, (guy shorts), kakis, LL Bean (especially the Bean Boots and blue and white checked sweater), ribbon belts, Brooks Brothers, Verne or Ray ban sunglasses, Timberland boots, Tretorns and and Sperry topsiders. Whales, ducks and the nautical theme were on everything from clothes to glasses. Mercedes, Volvo or BMW were and still are the cars of choice along with the Jeep Vagoneer with a wood panel which preceded today’s SUV. Older homes decorated in antiques and old chince were where they lived. Preppy names were popular. I even named my cat Muffy. Southern preps liked to “shag” to the 60’s oldies.

Today, my daughter, Caroline is also prep who attends The Norwood School in Bethesda, MD. Her friends belong to local country clubs with Chevy Chase Club being the preppiest, they attend Ms Simpson’s Dance Class which leads to cotillion and many summer in preppy locals like The Vineyard. Sports are still a popular past time for her group especially lacrosse, field hockey, golf and tennis. In the early 2000s Preppy again became mainstream. Stores such as American eagle and Abercrombie & Fitch (not to be confused with the original Abercrombie & Fitch that was a very expensive upscale store in the 1980s in Georgetown) were established. These stores are a more more sexy interpretation of preppy made for the common consumer and are not truly preppy. Caroline and her friends wears some of this stuff but prefers J Crew, the new Lilly Pulitzer (only recently started up again and more stylish), Vineyard Vines, Polo, Black Dog shirts, Lacoste (no longer Izod Lacoste), Tiffany silver, ribbon belts, head bands, CK Bradley (the new Pierre Deux), Eliza B flops, ribbons in their hair, colorful clear water bottles, canvas totes, clothes picked up from boutiques while on vacation or from private boy’s schools like Landon. The preppy designers go on and on and are more plentiful than in my days. In the DC area some younger preps occasionally spice up their wardrobe with designer duds like 7 for all Mankind and Juicy, but wear it in a more conservative way.

So, as time goes by and clothing styles change, for many the “preppy style” will go out of style again. For true preps it never goes out of style. Preppy means a happy, fun life as well as a great wardrobe!
Caroline, Sumner and Lisa look so preppy in their Lilly skirts and Eliza B flops.
by Holly S September 15, 2005
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A young person from a rich or well-off family who goes to an expensive school and/or who wears expensive, tidy clothes. Preppies are often mistaken for Valley-Girls; the annoying "LIKE, OH MY GOD!" people that prefer trends over class and make your skin crawl, and highschool popular kids, which are even worse because they are often rude and dress like sluts. True preppies are very nice and approachable down to earth people. They were raised well and are equiped with common decency and manners.
The Bush Daughters would be preppy if they would quit acting like morons.
by c'est julie July 20, 2005
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Someone who is preppy appreciates classic, conservative clothing. Contrary to popular teenage misconceptions, preppy people do not wear Abercrombie and Fitch, GAP, American Eagle; these clothes are trendy and entirely too flashy/showy for a true prep. Rather, traditionally preppy people wear Lilly Pulitzer, Polo Ralph Lauren, Lacoste, Brooks Brothers, or L.L. Bean. Preppy girls favor simple clothing and jewelry; polo shirts with the collar popped, simple sundresses with a cardigan tied round the neck, or ribbon belts. Preppy males also wear polo shirts with the collar popped, appreciate the simple polished asthetic of khakis, and generally do not dress like slobs.
"Doesn't Elizabth's pink polo shirt with the popped collar look nice?" whispered Robert, fingering his own khakis, and adjusting his tie.
by Pink and Green February 17, 2004
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preppy is someone who comes from a certain amount of wealth and is raised within a certain lifestyle. Although "being preppy" is often conceived as one dressing in polos and popping the collar, there are different ways to approach the idea. First off, typically, preppies lean to the conservative side never wearing anything that would by any means be provocative or sluttly. Classy, not cheap and not thrown together. Tradition not trends. True preps don't just enter the everyday mall and buy things from the mainstream chains where the business thrives on the "hot" new fashion. Old, well respected establishments is the way of life. Education is pivotal, although one does not have to attend a New England prep school to reach said status. There are exclusive suburban public high schools who are a breeding ground to the preppy lifestyle. Ergo,preps are not limited to the New England and even the Southern areas, the North Shore in Illinois is a good example of true preps outside the stereotypical locations. Some may say that preps are ALWAYS snots, but that is not ALWAYS true. Yes, some are type A snots and probably should be smacked, but some are actually caring, nice people. It's not like they are this superior race, they are like any other demographic, consisting of the brats and the down to earth. Being preppy isn't just dressing in pastels and popping the collar it's a way one lives day to day. It's a mindset, and the look a prep has is just a supplement to the pattern of life.
preppy is more than fashion, it's tradition and excellence and respectfulness and a way of life.
by KTWHIT June 20, 2008
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There are the private old school, polo shirt & loafer wearing preppies that summer in Nantucket and love sailing, rugby, squash, etc. Then there are the public school, mall shopping, Abercrombie and Finch wearing preppies who love football. You can even hear the difference in their grammar (Old school don't use valley girl as do public school) and speech. For instance when a person says apple, car and please. Old school would say "for instance", Public school says "like".

They are two different groups. Public school preps (PSP) have a tendency to "need" to point out to others they are popular while in high school. Where an old school prep (OSP) is concerned with family pride and life style that lasts into adulthood and until they die. True the OSP made say something not nice BUT they are polite most of the time. PSP often are rude to others. Want to get back at a PSP? Tell them they are not OPS which is what they are imitating whether they realize it or not. When they say they are, ask them when their family arrive in America was it over 200 years ago? Or when the last time they went sailing?

Preppy is slang for preparatory school. A pubic high school, though provides a good education, is not prep-school where students take college level classes. There should be two different names for old school prep (OSP) and public school prep (PSP).
OSP Girl: "Daniel, a PSP is waving at you." PSP Girl says to Nathanial: "Oh, My, God ! Dan, I have not seen you in sooooo long." Grabs at Daniel for a hug. Daniel unhappy but polite: "Hi, ah...Niki. What are you doing here?" "I can't believe I ran into you...OMG It is totally awesome to see you...Do you like my preppy new shoes?" OSP Girl: "Hello, I am sorry to interrupt your conversation but we are on our way to meet some of our friends. It was a pleasure meeting you." PSP: OMG it was totally awesome to run into you. We should get together. Wait let me send you a text."
by We Have Been Here March 10, 2010
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