Preppiest Books

Lisa Birnback:
The Official Preppy Handbook
True Prep: It's a Whole New Old World

F. Scott Fitzgerald: (All of his work but these in particular)
The Great Gatsby
This Side of Paradise 
The Beautiful and Damned

J.D. Salinger:
The Catcher in the Rye

Jane Austen:
Sense and Sensibility 
Emma
Pride and Prejudice
Northanger Abbey
Mansfield Park

John Knowles:
A Separate Peace 

Dominick Dunne:
A Season in Purgatory 

Edith Wharton:
The Age of Innocence

William F. Buckley Jr.:
God and Man at Yale

Nelson W. Aldrich:
Old Money: The Mythology of America's Upper Class

Dave Eggers:
A Heartbreaking Work of Staggering Genius

Charles Dickens
Great Expectations

Wendy Wasserstein:
Elements of Style: A Novel

Oscar Wilde:
The Importance of Being Earnest

Tobias Wolff:
Old School

Richard Yates:
A Good School
Revolutionary Road

Paul Fussell:
Class

Thomas Shomo:
To Manner Born, To Manners Bred

Preppiest Sports

Crew/Rowing

Sailing

Squash

Golf

Tennis

Field Hockey

Lacrosse

Rugby

Skiing

Ice Hockey (Only during prep school)

Badminton (For recreation)

Equestrianism (Dressage, Jumping, etc.)

Polo (To watch)

Soccer

Football (To play through prep school and to watch)

Honorable Mentions:
Swimming
Broomball
Croquet
Track and Field
Fencing

The 50 Preppiest Movies and TV Shows

Follow the link below for this IMDB list.

http://www.imdb.com/list/ls071449123/

Preppiest Colleges & Universities in America

After lots of research and college visits, I have compiled a list of what I believe to be the preppiest colleges in the United States. This list is in alphabetical order.

Boston College
Best For: The Catholic Preppy

Bowdoin College
Best For: The Athletic Preppy

Colgate University
Best For: The Preppy that isn't looking for a "suitcase school."

College of William & Mary
Best For: The Preppy looking for a medium-sized state school with history.

Dartmouth College
Best For: The Insanely Smart, Outdoorsy Preppy.

Duke University
Best For: The Insanely Smart, Athletic Preppy.

Georgetown University
Best For: The Smart, Politically Active Preppy.

Hampden-Sydney College
Best For: The Souther Preppy Guy looking for a finishing school as much as a college.

Miami University, Oxford, Ohio
Best For: The Preppy looking for a traditional state college experience with attractive, J. Crew loving students.

Princeton University
Best For: The Most Intelligent, Tradition-Loving Preppy that is most likely a legacy.

Southern Methodist University
Best For: The Conservative, Attractive, Texas-Loving Preppy.

University of Virginia
Best For: The Intelligent Preppy looking for a big, traditional state school.

Vanderbilt University
Best For: The Well Rounded Preppy looking for the "Harvard of the South."

Wake Forest University
Best For: The Hard Working Preppy looking for a traditionally preppy environment.

Washington and Lee University
Best For: The Preppy looking for a small, traditional university full of good ol' boys and gals in a quaint town.

Honorable Mentions:
Babson College
Davidson College
Elon University
Harvard University
Middlebury College
Pepperdine University
Sewanee - The University of the South
Texas Christian University
Trinity College
University of North Carolina, Chapel Hill
University of Richmond
Williams College
Yale University