One Year: Ten Preppy Books

Thank you to Kate with Nautical by Nature for this guest post on some of the best preppy books in every genre. Visit Nautical by Nature to read more by Kate and for great tips on everything preppy and nautical—from clothing to home décor!

Last year, I rejoined my local public library and have been taking advantage of this amazing (free) resource. Here is a list of the top ten preppy books I read in 2011. From fictional stories of life on the Upper East Side to candid photos of preppy Ivy League style, these books will be your guide to all things prep.

1. True Prep: It’s a Whole New Old World by Lisa Birnbach and Chip Kidd

The new Bible for the preppy kids of today, this book is the follow up to the Official Preppy Handbook published in 1980. Updated to include the preppy take on everything from reality TV to PDA.

"True Prep: It’s a Whole New Old World" by Lisa Birnbach and Chip Kidd

2. The Ex-Debutante by Linda Francis Lee

A former Texan must return to her old money roots and Willow Creek high society following her mother’s most recent divorce (No. 4). Carlisle is thrown back into the life she thought she had escaped: family secrets, Southern bad boys, and a debutante ball, oh my!

"The Ex-Debutante" by Linda Francis Lee

3. The Secret Lives of Dresses by Erin McKean

Each dress in Mimi’s vintage clothing store has its own story to tell. When Dora returns to her hometown in North Carolina, she takes over her grandmother, Mimi’s, store. Hidden in the pocket of each dress, Dora discovers the hand written stories of the dresses her grandmother loved so dearly.

"The Secret Lives of Dresses" by Erin McKean

4. Take Ivy by Shosuke Ishizu  

This book was originally published in Japan in the 1960s and then translated into English in 2010. Candid photos of men on the campuses of American Ivy League universities, Take Ivy is a look at the preppy men’s fashion of the 1960s through the eyes of four Japanese sartorial style fans.

"Take Ivy" by Shosuke Ishizu

5. Prep: A Novel by Curtis Sittenfeld 

Prep is about a young teen from the Midwest finding herself at an elite boarding school in Massachusetts. She is not sure where she fits in with her fellow classmates who are from privileged backgrounds that seem like a foreign world to Lee.

"Prep: A Novel" by Curtis Sittenfeld

6. The Overnight Socialite: A Novel by Bridie Clark

The Eliza Doolittle of the twenty-first century, Lucy Jo is transformed into Manhattan’s “it girl” by handsome Upper East Side bachelor Wyatt Hayes. This novel is a peek into what it takes to be part of Manhattan’s elite from the perspective an outsider turned insider.

"The Overnight Socialite: A Novel" by Bridie Clark

7. The Ivy Chronicles by Karen Quinn

After losing it all (Upper East Side apartment, wealthy husband, and job), Ivy must figure out how to support herself and two daughters. Ivy opens a consulting business to help the children of Manhattan’s elite get into the city’s most selective preschools. Imagine Gossip Girl with toddlers!

"The Ivy Chronicles" by Karen Quinn

8. Preppy: Cultivating Ivy Style by Jeffrey Banks 

This book presents the history of the preppy look: how it evolved over time and what influenced the preppy movement. Using photos from advertisements and personal collections, it takes the reader through the early years of the American preppy style up to the revival of the movement in the 1980s and today.

"Preppy: Cultivating Ivy Style" by Jeffrey Banks

9. American Wife: A Novel by Curtis Sittenfeld

Loosely based on former First Lady Laura Bush, American Wife is the story of a woman that marries into a political family. Quickly propelled into a life of privilege, main character Alice must balance her own views with that of her conservative husband.

"American Wife: A Novel" by Curtis Sittenfeld

10. Confessions of a Prep School Mommy Handler: A Memoir by Wade Rouse

This book is a hilarious look at the queen bee mothers at a private school from the perspective of the school’s director of public relations. The characters are over-the-top, “mean mommies” that demand the very best for their privileged offspring.

"Confessions of a Prep School Mommy Handler: A Memoir" by Wade Rouse

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