Madras men, part of the Deerfield Academy graduating class of 1961

Preppy: Cultivating Ivy Style is no tongue-in-cheek preppy handbook. It is an encyclopedia of prep—with a foreword by Lilly Pulitzer, no less—filled with camp photos. We chuckled while paging through True Prep, the newest version of The Official Preppy Handbook by Lisa Birnbach. Preppy, the work of Jeffrey Banks and Doria de La Chapelle, lies at the other end of the spectrum, a coffee-table showpiece and a must for both old-school preps (whose Ivy League-schooled ancestors may be pictured) and prep wannabes like the rest of us.

Banks, a fashion designer, fell in love with the style as a teen while working at Britches of Georgetown. While studying at Pratt and Parsons, he was invited by friends to visit Watch Hill, Rhode Island, aka prep nirvana. De La Chapelle, who also wrote the book Tartan with Banks, is a bona fide East End prep and a Skidmore College graduate who belongs to several clubs in the Hamptons. “Sag Harbor is preppy and Southampton is preppiest,” says Banks. “East Hampton has prep enclaves.” (Shelter Island, of course, deserves honorable mention.)

East End Prep At Its Best
What defines East End prep? “Valerie Smith’s little monogram shop on Newtown Lane in East Hampton,” says de La Chapelle. “The American Hotel is heaven. People really dress for lunch at the Southampton Bathing Corporation; Maidstone is more casual. People come down to lunch by the beach in their tennis clothes or with a shirt over a swimsuit top. Few of us wear hats. But men really are required to wear collared shirts on the tennis court. And, yes, you will see 25-, 30-year-old madras shorts.”

When it comes to preppy fashion, both have their favorites. “Brooks Brothers was an architect of preppy style,” says Banks, who also gives a nod to Ralph Lauren, J.Crew and Southampton’s J. McLaughlin (a haven for “the cashmere sweater”). “Tom Browne goosed up that look, and more recently Band of Outsiders and Michael Bastian.”

“Lilly Pulitzer is a wonderful resort look,” says de La Chapelle. Jack Rogers, Tory Burch (“the evolved preppy look”), Jack Wills in Southampton (“a British store that has a cheekiness to it”) and Stubbs & Wootton all win points as well.

De La Chapelle says the word “preppy” entered into common parlance when the film Love Story debuted in 1970. Banks—whose zenith prep moment came when Prince Charles wrote to thank him for a copy of Tartan—remembers the lifestyle as a rarefied one. “It was once a very exclusive, tweedy club,” he says. “But now anyone who has the money can wear white linen pants, a navy blazer and no socks.”

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