The Top 40 Culturally Relevant Preppies

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Ladies, locate your tennis skirts. Gents, dig up those Nantucket red pants. The New York Times and The Awl have called it: Preppie chic is back. We’ve seen this coming since Vampire Weekend hit the indie big-time back in 2007 and, frankly, have been trying the head it off at the pass ever since. But sometimes, when you can’t beat a trend, you just have to revel in it. So, in celebration of all things square and Country Club-approved, we have created a handy guide to the top 40 (get it?) most culturally relevant preppies. Let us know who your favorite popped collar-wearing Young Republican (or, as it turns out, Democrat) is in the comments.

1. Zack “Preppie” Morris (Mark-Paul Gosselaar), Saved by the Bell

2. Vampire Weekend

3. The Heathers, Heathers

4. Robert Chambers, “The Preppie Killer”

5. Carlton Banks (Alfonso Ribeiro), The Fresh Prince of Bel-Air

6. Prince William and Prince Harry

7. Tucker Carlson

8. Angela Bower (Judith Light), Who’s the Boss?

9. Tiger Woods

10. Prep-Unit (Tea Party rap)

11. Dave Matthews

12. The Dead Poets Society kids

13. Ralph Lauren

14. Phineas, A Separate Peace

15. Cecile (Selma Blair), Cruel Intentions

16. Gordon Gekko (Michael Douglas), Wall Street

17. Pete Campbell (Vincent Kartheiser), Mad Men

18. Chris Wilton (Jonathan Rhys Myers), Match Point

19. Lilly Pulitzer

20. Tom Ripley (Matt Damon), Marge Sherwood (Gwyneth Paltrow), Dickie Greenleaf (Jude Law), The Talented Mr. Ripley

21. Cordelia Chase (Charisma Carpenter), Buffy the Vampire Slayer

22. C.C. Babcock (Lauren Lane), The Nanny

23. Patrick Bateman, American Psycho

24. The Bush twins

25. René Lacoste

26. Martha Stewart

27. Brooke Shields

28. JFK

29. Leslie Hunter (Ally Sheedy), St. Elmo’s Fire

30. Tory Burch

31. Chuck Bass (Ed Westwick), Gossip Girl

32. Lisa Birnbach, author of The Preppy Handbook and the forthcoming True Prep

33. Steff (James Spader), Pretty in Pink

34. Louis Winthorpe III (Dan Aykroyd), Trading Places

35. Jennifer (Ali MacGraw) and Oliver (Ryan O’Neal), Love Story

36. Huey Lewis and the News

37. The kids of Metropolitan

38. Omega Theta Pi fraternity, Animal House

39. Alex P. Keaton (Michael J. Fox), Family Ties

40. Barack Obama