The Official Preppy Handbook

By: Lisa Birnbach

Originally published in 1980, this is a primer on how to dress like classic preps like John F. Kennedy or Carlton Banks. Forget the recently-published sequel and go with the original. From boat shoes to khakis, this is the book that teaches how you to rock a navy blazer correctly. It also serves a great guide on the sorts of stuff you can get from shops like L.L. Bean, Brooks Brothers, and Lacoste.