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30+ Very Preppy Movies with the Preppiest Characters

Updated February 26, 2020 1.9k votes 254 voters 15.8k views43 items

We can't all live like the rich, but we can get a glimpse into the world of the preppy elite through great films. Very preppy movies with characters who went to prep school or living the prep life feature all of the relationship drama, desperation, and struggle we all experience in life – but their characters are typically much cleaner cut, in oxfords, khakis, sweaters, and somehow always ready to step onto a sailboat, even during tragedy. This is a list of great preppy movies, featuring everything from The Great Gatsby to Love Story to Ordinary People.

What films will you find on this list of the preppiest movies? Any adaptation of The Great Gatsby has to make the cut. Whether you prefer Robert Redford or Leonardo DiCaprio in the title role, this classic preppy tale is undeniably a classic. The Ice Storm is another good movie with a preppy aesthetic and impeccable acting. The Graduate follows a recent college graduate as he enjoys the luxuries of preppy life – and a scandalous love affair – while wiling the days away as only the wealthy can. Other films featured on this top preppy movies list include Rushmore, Good Will Hunting, and The Social Network.

Which movie do you like the best? Give your favorites a thumbs up and please add any good films featuring preppy characters that are missing.

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