preppy
A guy or girl who dresses perfectly without trying to. They appear to do everything well and with ease. They are frequently the descendants of "old" money and are very well off financially. Despite this, they don't need obsequious displays of wealth (i.e. wearing Versace) to convey that they are better off than everyone else. The usual clothing of choice is Lacoste, Ralph Lauren, Lilly, L.L. Bean, J. Press, and Brooks Brothers to name a few. Abercrombie & Fitch is *not* a preppy staple, as it has been co-opted by the nouveau and hoi polloi. Connecticut has more preppies per square mile than any other state (i should know, i was born and raised there, a child of privilege). The highest concentration of them are on Connecticut's "Gold Coast", Westport, Darien, New Canaan, with smaller yet densely clustered habitations in Madison, Clinton, Guilford, West Hartford, Glastonbury, Farmington, Avon, Old Saybrook and Stonington. No, East Lyme isn't preppy, they're poseurs, simply nouveau riche trash flaunting daddy's hard-earned money. Preppies aren't snobs, per se, they simply don't wish to waste their intellect and humor on a lesser being, hence the popular notion of their being snobs. They simply have their style, mannerisms, codified behavior and traditions. One cannot be a preppy unless you are born into this station in life. Don't worry poseurs; they real preps can see through your pretenses, false as they are. They vacation in places not likely to be frequented by trash or nouveau riches, so they revel in places such as Martha's Vineyard, Block Island, Fisher's Island, Hilton Head Island and Sanibel Island. To the trained eye, once can identify a Connecticut preppie immediately. Because, quite simply, Connecticut preps are top shelf. It's key.
The place: The Caribe Hilton, San Juan Puerto Rico. The date: Christmas Eve, 2004 The scene: the bar/club at the Caribe Hilton. A large group, a family walks into the club, ages ranging from early teens to adults in their 50's. They are all clad in pastels, khakis, collars popped up, the Polo horse insignia emblazoned on all of their shirts, no noticeable makeup on the females, conservative hair styles for the males and females, they all have a healthy glow to their perfect caucasian complexions. They sit at a table and appear to enjoy themselves immensely. Theirs is a clubby, exclusive circle that cannot be penetrated or imitated by wannabees or other covetous outsiders. An onlooker in the club turns to his wife and comments: "Where are THEY from?" His wife replys, matter of factly, "From Connecticut, dear, can't you tell?"
By Preppy in Connecticut