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
a lot of these people are right, but a lot are wrong...I'll set the record straight...this definition comes from a TRUE prep-one who has summered in Nantucket for 12 years, and who goes to a top New England boarding school. A prep is usually waspy, but doesn't have to be. Some of the peppiest people I know live "new money" communities like Potomac, MD and Chevy Chase, MD. Preppiness is not just a particular clothing style, it is a lifestyle as well (I know everyone on here says that, but it's true). A preppy guy wears Vineyard Vines boxers, belts, and ties, Patagonia and The North Face fleeces, Birkenstock clogs, Rainbow and Reef flip flops, J Crew pants and critter shorts, Ralph Lauren seersucker/embroidered pants, Brooks Brothers ties and blazers, Ralph Lauren polo and oxford shirts in literally every color, a favorite is lime green with a pink Polo player icon, CK Bradley/CJ Laing/J. McLaughlin/Maax ribbon/needle pointed belts, Tiffany and Co monogrammed money clips and belt buckles, North Face backpacks, Ralph Lauren chino shorts and cable knit cashmere sweaters, LOTS of Lacoste shirts and Lacoste rugbys, Ralph Lauren rugbys, L.L. Bean Boots and moccasins, and Lilly Pulitzer/CJ Laing ties and bathing suits (yeah they're bright and kind of fruity, but that’s the point). Also worn are Sperry topsiders and Barbour jackets. Aviator sunglasses complete the look. Preppy girls dress basically the same as the guys, with some more designer items, like Seven jeans and Gucci sunglasses/horse bit loafers. Preps don’t always pop their collars, as now absolutely everyone is doing it in a vain attempt to be truly preppy. Sweaters are still tied around the neck, but less frequently. Preps would never go to a mall, and if that is the only shopping center near by, then Neimans and Saks are ok. Americana Manhasset is the only acceptable “mall,” if you will.
One thing that irritates me is when snotty Abercrombie wannabe preps call themselves preppy just because they wear a trashy shirt and like pink shorts. That stuff can make someone look put together, but it’s not preppy. Favorite prep activities include hunting, tailgating, playing tennis/lacrosse/sailing/squash/field hockey. Another prep pastime includes getting drunk on the vodka from Daddy’s liquor cabinet or sneaking some at the club. Preps summer in Maine, Nantucket, Martha’s Vineyard, and sometimes travel abroad. Preppy colleges include Princeton, Yale, Harvard, Dartmouth, Trinity, Colorado College, Bowdoin, etc. Preps grow up and marry other female preps who are like them. Preps are really nice, get to know some and you’ll see. They are never snobby, the snobby people are the fake preps who blast rap and drive around in heinous “tricked out” cars and wear Abercrombie, the skankiest brand at the mall. So go to a Dave Matthews or OAR concert, take a trip to Nantucket, or just walk down the street, and you will encounter some really nice preppy people.
Biff walked into class late, but he looked awesome in his seersucker shorts, Rainbow flip flops, Maax belt, and Ralph Lauren polo shirt.
by A. Wasp February 09, 2005
Preppies are people who go to prepatory highschools (Groton, Hotchkiss, Philips Exeter, Philips Andover, Deerfield, Laurence, etc.). Most of them shop at J. Crew, Banana Republic, Brooks Brothers, L.L. Bean, Ralph Lauren and all designer stores. Preppies are often mistaken for kids who shop at Abercrombie & Fitch, American Eagle Outfiters, Rave, etc. Those who think "preppies" are girls who shop at those stores are VERY wrong.
You could tell by the way they were clad in Brooks Brothers that they were utter preppies.
by BcBK March 16, 2006
As a public school teacher, I can speak to this topic with some authority. The term "preppy" originally described members of old-money patrician families with traditional ties to private bording schools. They live on the East Coast or in the South, and they can afford to "summer" places.

At their best, true preps preserve the best traditions of Western Civilization. They try to be honest, humble, brave, principled and public-spirited. They wear simple, elegant, well-made clothing, and they wear it until it falls apart. The manufacturer is unimportant; true preps respect good craftsmanship, not expensive pricing. Although they wear the Classic American Wardrobe, they realize that they did not invent it (except for boat shoes... your grandfathers DID invent boat shoes), and they have no exclusive claim to it.

Classic preps with noteworthy ancestors see their forebears as people to be lived up to, rather than people to be bragged about. They recognize their privileged status, and they work to become worthy of it.

Classic preps work hard to develop both mind and body; achievement in both the classroom and on the athletic field are highly valued.

At their worst, preps are snobs. They take pride in money they didn't earn, power they don't deserve, and people they don't value. When they die they leave behind them an ocean of gin and tonic, a garage full of fine automobiles, a fantastic wardrobe, and a wasted life. It is good to appear in their will, but bad to appear in their presence.

Nowadays, though, the term commonly describes the upper strata of "popular" kids in many American highschools. I would argue that since this group vastly outnumbers traditional preppies, they perhaps have staked a greater claim to the word.
See that kid with the black pants, the nose ring and the mohawk? Instead of shoving him into a locker, I think I'll introduce myself and shake his hand, because I'm a true preppy.
by David Medlock August 22, 2005
I grew up around many true preps and liked most of them. I'm 45 and when we were teens we wore madras pants, B.Bro oxfords, Izod underneath (popped)and Weejuns with 1/10 Krugerands in the penny slots, no socks. We shopped at either Belks or Collins (Bruce and Allen Collins were text book preps)drank cheap beer and and chased tale like every other guy. The tale we were chasing was very elusive prep girls. (Not party prep A&F girls like nowdays, the real refined kind)We did our partying at Ocean Drive Beach S.C. during graduation (anybody's graduation) but we summered in the OBX or Litchfield where the people like us were also summering.
Chip and Bruce are meeting us at The Pad at ten'ish. He said to stop at Hardwicks on the way, cause we were going to a party the Sigma Chi girls were throwing at Cherry Grove. Don't wear those garish sandles, wear your loafers. I'm wearing my new madras shorts and ox thats a little big on me.Don't wear that damn Rolex, you look like a pimp, you can wear my Timex if you have to know the time. Later Gator.
by Charlie January 19, 2005
A prep...someone who is classy and classic, not too showy or they would not be a prep, generally from the new england area, but can also be from the south, usually from a private "prep" school like Woodberry Forest or Baylor or Harpeth Hall, girls dress incudes polos, khakis, cardigans, floral dresses, cable knit sweaters, from places like polo, lilly, jcrew, and ck bradley, they carry tote bags with their monograms from llbean , wear pearls and silver monogram jewelry, wear ribbon belts from eliza b, and do not dress slutty in any way, boys wear polos, khakis, madras print shorts from banana, polo, jcrew, and nantucket reds, jackets from the north face, flip flops from rainbows, scruffed up baseball caps, the color code for both includes bright colors like pink, green, purple, and yellow, they are generally smart and nice and from a good, well-established family, they get into selective, private colleges, they sail, play tennis, golf, and swimming, as well as lacrosse and field hockey and sometimes soccer
Hey Muffy, I just bought a new lilly to wear to the club this Sunday!
by Ellie April 15, 2005
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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