Book Review: Preppy

I like cardigans—a lot. And I have a particular weakness for the camel-coloured wool variety. My penny loafer collection is gaining ground. I find argyle bowties to be the perfect accessory. It’s time to come clean: My name is Jenny and my wardrobe is heavily under the influence of prep. And while pearls may not win any attention in a crowded bar, Jeffrey Banks and Doria de la Chapelle’s Preppy: Cultivating Ivy Style helped me feel more loving towards the boring (I mean classic) garments that have overrun my closet. Their book explores the roots and history of the classic collegiate look and its evolution into a clean-cut staple that’s, well, kind of everywhere.

The book has the basics to share: prep was born and bred in the early 1900s by Ivy League boys on the East Coast who paired athletic clothes with refined classics and emblems of their school pride (pins, ribbons, badges). To be a true prep, conformity was key, and often membership to the exclusive clubs came down to getting the details just so, like the roll of a cuff or the colour and print of your necktie. By the 1930s, the style was adopted by women and quickly spread to the leisure loving upper class who wore kooky, clean-cut frocks to Palm Beach and the golf course. In the book Thrift Score, Al Hoff perfectly describes some of prep’s most iconic looks, when she suggests throwing a preppy themed party where attendees should don “blazers, madras shorts, polo shirts (Lacoste only please, Ralph Lauren is an interloper), green belts with whales, monogrammed crewneck sweaters with a pattern of little ducks,” and anything nautical.

Preppy frequently repeats that prep is a way of life. For many, getting it right was less about what you wore, but rather how you wore it. Pairing the pearls with an “air of complete and utter nonchalance,” for example. The Kennedys became a symbol of true prep by exuding “the fun-loving youthful air of perennial college students.” The authors explain, “The ease and carelessness with which they wore their clothes was as attractive as the clothes themselves.”

The book is divided into seven chapters detailing prep’s evolution, and is accompanied by many large and striking photos from history and pop culture. It outlines how influencial prep has been, referencing the grey flannel suit, attire in Mad Men, movies like The Graduate, Love Story, and Annie Hall, and advertising stunts like Tommy Hilfiger’s “dysfunctional family” campaign inspired by The Royal Tenenbaums. I like that the book didn’t just pay homage to the stuffy and static beginnings of prep, when only the rich and Waspy could sport the clothes. It also shows how it emerged from prep schools to include a diverse, multi-ethnic, pan gender crowd in 2012.

Tommy Hilfiger explained, “The future of preppy is evolution—retaining its heritage, but twisting and shaping it to new audiences.” I’m glad that in the 21st century there is more than one way to engage with the style, and more than one kind of person who can wear it. Lately, I’m leaning towards preppy with a twist. An Amy Winehouse crashes Harvard thing, pairing big hair, exaggerated makeup and leopard prints with cutesy cardigans and penny loafers. I’ll just save my tartan pants for another day.

Preppy: Cultivating Ivy Style by Jeffrey Banks and Doria de la Chapelle. Rizolli Press, 2011
Reviewed by Jenny Morris

2 thoughts on “Book Review: Preppy


    When I started grade nine, I had to choice between going to the country high school my sibs went to, or the Catholic school an hour’s bus ride away. As soon as I saw those navy-and-grey uniforms, with the pleated skirts and crested blazers, an extra 45 minutes on the bus seemed totally worth it.


  2. Love everything about this!

    @g. I went to a catholic school too but blazers weren’t a part of our uniform, so I wore my own to school and had to go to detention a couple of times because of it, hah

Leave a Reply

Your email address will not be published. Required fields are marked *

You may use these HTML tags and attributes: <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <strike> <strong>