The term "preppy" has been twisted in recent times. Preps have gotten a bad reputation through TV shows, movies, and books. For generations "preppy" has been a term that describes a certain lifestyle. Most recently, "preppy" has come to signify a group of people in high school who wear clothes from Hollister, American Eagle, and Abercrombie and tend to had a snotty and mean streak.
In reality, preps are usually WASPS from old money. They consider themselves to be the epitome of classy. They wear classy and timeless clothes from stores like Vineyard Vines, J. Crew, Lacoste, Ralph Lauren, and Brooks Brothers. They seldom take risks with their clothing choices or jewelry and they tend to ignore current fashion trends.
Northern Virginia, Connecticut Massachusetts, Vermont, North Carolina, Rhode Island, and New Hampshire tend to be the "preppier" states. Their homes are well sized, but far from ostentatious. Preps make a huge effort to avoid showing off their money: they are instead secure with what they have.
Preppy sports tend to be the more expensive sports. Lacross, field hockey, swimming, rugby, tennis, golf, and horseback riding are all considered to be "preppy sports."
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A preppie is a person whose manners and dress are typical of a traditional preparatory (private) school.