This book written in 1980 says that the Preppy outlook is timeless. As a non-prep, I can't vouch for all the features, but as for clothes and jobs it still holds true. Putting aside all the details in this book (which are many) is a certain "je n'est ce what the f*ck" unique to the preppy worldview that this author has revealed.
As for clothes, J.Crew 25 years later still features the same Fair Isle sweaters, the hot pink and lime green striped grosgrain belts, the loud print skirts (small prints are considered "ditsy"), and the embroidered repeating motifs on pants. All of these things that I just thought were... ugly, actually are quintessential preppy style.
October 18, 2005
For some reason, I was just thinking about "The Preppy Handbook," which came out a quarter century ago. Do people still read it? Checking Amazon, I see they do. There are many five-star reviews from within the last year (even though you can't actually buy the book on Amazon). An example: