Listmania!
Pretend You're A Preppie
By an Amazon.com customer
The Official Preppy HandbookThe Official Preppy Handbook by Jonathan Roberts
Buy used from: $3.66
Aka, THE Handbook.  It's key.
Emily Post's Etiquette, 17th Edition (Thumb Indexed)Emily Post's Etiquette, 17th Edition (Thumb Indexed) by Peggy Post
Buy new: $27.04 / Used from: $23.26
Preppies are polite...
Better than Beauty: A Guide to CharmBetter than Beauty: A Guide to Charm by H Valentine
Buy new: $10.17 / Used from: $4.47
...and charming.
The Official Sloane Ranger Handbook: How The British Upper Class Prepares Its Offspring For LifeThe Official Sloane Ranger Handbook: How The British Upper Class Prepares Its Offspring For Life by Ann Barr
Buy used from: $59.44
If you think NEW England is preppy, think again...
The English Gentleman (Prion Humour Classics)The English Gentleman (Prion Humour Classics) by Douglas Sutherland
Buy used from: $36.90
...and get to know your roots.
BCBG: Le guide du bon chic, bon genre (Collection "Les Guides Herme") (French Edition)BCBG: Le guide du bon chic, bon genre (Collection "Les Guides Herme") (French Edition) by Thierry Mantoux
Buy used from: $8.86
Pour meilleur comprendre vos equivalents francais...pour etre comme il faut.
Tipsy in Madras: A complete guide to 80s preppy drinkingTipsy in Madras: A complete guide to 80s preppy drinking by Matt Walker
Buy used from: $59.92
Despite the subtitle, it's timeless...
The Bartender's Bible: 1001 Mixed DrinksThe Bartender's Bible: 1001 Mixed Drinks by Gary Regan
Buy new: $17.09 / Used from: $0.01
Your new encyclopedia.
The Wasp CookbookThe Wasp Cookbook by Alexandra Wentworth
Buy used from: $41.78
Ignore the recipes, absorb their introductions.
Private Secondary Schools 2004-2005Private Secondary Schools 2004-2005 by Peterson's
Buy used from: $1.99
You can never...
The Best Private High Schools and How to Get In, 2nd EditionThe Best Private High Schools and How to Get In, 2nd Edition by Frank Leana Ph.D.
Buy used from: $85.70
...start too soon.
Barron's Guide to the Most Competitive CollegesBarron's Guide to the Most Competitive Colleges
Buy used from: $0.01
Can't go wrong with East Coast, private, prewar  (Revolutionary War, that is...)
A Separate PeaceA Separate Peace by John Knowles
Buy new: $8.64 / Used from: $0.01
Prep lit at its best.
The Stories of John CheeverThe Stories of John Cheever by John Cheever
Buy new: $12.21 / Used from: $7.53
This stuff is hardcore.
Colonial StyleColonial Style by Treena Crochet
Buy new: $19.77 / Used from: $9.95
To inspire you...
Virginia Plantation HomesVirginia Plantation Homes by David King Gleason
Buy new: $36.46 / Used from: $26.89
...some more.
Essentially Lilly: A Guide to Colorful EntertainingEssentially Lilly: A Guide to Colorful Entertaining by Lilly Pulitzer
Buy new: $22.80 / Used from: $3.65
Insights from Lilly, Our Lady of Perpetual Prep.
Welcome to the Episcopal Church: An Introduction to Its History, Faith, and WorshipWelcome to the Episcopal Church: An Introduction to Its History, Faith, and Worship by Christopher L. Webber
Buy new: $10.08 / Used from: $2.99
Because the pope is not a preppie.
A Southern Belle Primer: Why Princess Margaret Will Never Be a Kappa Kappa GammaA Southern Belle Primer: Why Princess Margaret Will Never Be a Kappa Kappa Gamma by Maryln Schwartz
Buy new: $9.56 / Used from: $0.01
Concerning your Southern breed of prep.
An American ChildhoodAn American Childhood by Annie Dillard
Buy new: $10.07 / Used from: $0.01
Miss out on a preppy childhood?  Read this and relive the memories you never had!
The Big House: A Century in the Life of an American Summer HomeThe Big House: A Century in the Life of an American Summer Home by George Howe Colt
Buy new: $10.17 / Used from: $0.01
Because "summer" is more than a noun.