Definitions

from The American Heritage® Dictionary of the English Language, 4th Edition

  • n. Informal A student or former student of a preparatory school.
  • n. Informal A person whose manner and dress are deemed typical of traditional preparatory schools.
  • adj. Of or relating to a preppy or a preparatory school.

from Wiktionary, Creative Commons Attribution/Share-Alike License

  • adj. relating to things (such as clothing) that are typical of students at prep schools

Etymologies

prep(aratory school) + -y1.
(American Heritage® Dictionary of the English Language, Fourth Edition)
prep +‎ -y, with a doubling of the p to ensure proper pronunciation. (Wiktionary)

Examples

  • One of the six "gangs" of girls Mr. Roth plans to send down the runway this season is named the "Twill Seekers," whom he describes as preppy, Upper East Siders who wear items such as this striped rugby wrap dress.

    Fashion Look Book: Christian Francis Roth

  • The oddity of my elementary school situation was that those who ruled classroom society were what would be called preppy.

    Steve Bergsman's 'Growing Up Levittown': 'The Hop,' An Excerpt

  • Until the 1980s, a California preppy was all but oxymoronic.

    California Dreamers

  • I mean, your band, obviously, has been referred to as a preppy band, a bunch of privileged kids, you know, trying to be punkers.

    Vampire Weekend: Beyond The Blogs

  • And so one day, as I trotted along Madison with my understated in style but not in price bag in the crook of my arm, an inevitable question popped into my head: which perfumes can be described as preppy?

    In Which I Am Being Preppy

  • GRACE: And tonight, the so-called preppy killer made headlines after strangling a teenager in Central Park, blaming her death on "rough sex."

    CNN Transcript Oct 23, 2007

  • The so-called preppy killer -- remember Robert Chambers -- well, he ` s headed back to jail.

    CNN Transcript Jul 13, 2005

  • PAULA ZAHN, CNN ANCHOR: After 15 years behind bars, Robert Chambers, the so-called preppy killer, is free.

    CNN Transcript Feb 14, 2003

  • JASON CARROLL, CNN CORRESPONDENT (voice-over): It was known as the preppy murder.

    CNN Transcript Feb 14, 2003

  • Too scruffy even to be called preppy, the young Grace Kelly liked to dress down, perhaps as an apology for those looks.

    Top stories from Times Online

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