The preppy handbook

PREPPY: CULTIVATING IVY STYLE

By Jeffrey Banks & Doria de la Chapelle for Rizzoli New York, 169 pages

Available at National Book Store

The word “preppy” conjures images of Ivy League students — of polo mallet-hitting, paddle-pushing, golf club-swinging and tennis racket-smashing WASPs (White Anglo-Saxon Protestants) in classic, clean-cut clothes; young men of genteel backgrounds and wealth from exclusive enclaves like Connecticut, Palm Beach, Newport and Nassau, to name a few.

Originally called “Ivy style,” this fashion term changed after Ali MacGraw, portraying a Radcliffe student, called Ryan O’Neal, her Harvard-schooled boyfriend, “preppy” in the classic ’70s movie Love Story.

Madras men: Part of the Deerfield Academy graduating class circa 1961 in their Madras jackets, a sweeping Ivy trend in the ’50s and ’60s.

Ivy style first surfaced in the East Coast of the United States in the 1920s after the First World War; it was the attempt of elite Princeton campus-attending young men to distinguish themselves from other university-going students by their manner of dressing. Their ideal of style combined good breeding with quirky collegiate dressing and living — representative of idyllic college days, sports, and the spirit and vitality of youth. They paired athletic clothing from the playing fields with street wear typically accessorized with caps, ties, and pins signifying membership to prestigious clubs.

The appeal of Ivy style quickly spread across other elite schools like Harvard and Yale; even the women who went to prestigious, all-girls schools caught the Ivy-style fever and borrowed their brothers’/boyfriends’ sweaters and sports jackets. F. Scott Fitzgerald, the famous writer and Princeton graduate, celebrated and detailed the Ivy League style in his first book This Side of Paradise.

J. Press and the more influential American clothing institution Brooks Brothers were the earliest purveyors of Ivy style (1902). They created an elegant and unique preppy style of clothing that was all about the details — the shirt cuff with a button or two, the sports coat with one or three buttons, Peter Pan collars, perfectly tailored tweed or wool jackets, fitted Madras blazers and Shetland crewneck sweaters. Brooks Brothers’ soft-shoulder suits, diluted double-breasted polo coat with mother-of-pearl buttons in creamy white, gray and camel and the classic button-down shirt in Blue #3 were the early hallmarks of preppy style. In 1939, GH Bass introduced penny loafers, which, together with the rubber-soled athlete shoes of white buckskin, heel-less golf shoes, and two-toned saddle shoes became integral parts of the preppy look.

Preppy in the movies: Katharine Hepburn was a poster girl for the preppy look, here showing off her argyle in 1952.

In 1949, Ivy style formally became a unisex fashion trend; Brooks Brothers launched the “pink buttoned-down shirt” and female students from Vassar, Bryn Mawr, Wellesley, Smith, Radcliffe and Mt. Holyoke made a beeline for the shirt, together with the McMullen mini-cable cardigan, cashmere sweaters, wrap skirts, Madras short waist dresses and softened oxford shirts. Women adorned their Ivy outfits with “it” jewelry like pearls (preferably inherited), along with gold charm bracelets; they accessorized them with triangular cotton scarves, Capezio ballet shoes, Navajo sandals and Pappagallos loafer-shaped slip-ons. By 1959, Brooks Brothers outfitted their stores with fitting rooms for women.

Preppy did not remain an exclusive college-campus style for long; Hollywood celebrities, professional athletes, politicians, businessmen and socialites embraced the classic American style soon afterward. Katharine Hepburn took her argyle sweaters and tweed skirts to the golf course, Grace Kelly packed her cashmere twin sets to movie sets and cruises; Cary Grant, Clark Gable and Gary Cooper wore handsome, tailored and powerful suits in their movies. Jackie Kennedy rode her horse and attended socials in true preppy form; her future husband, John F. Kennedy, wore button-down shirts and khakis on vacations in Maine and white oxford shirts and Repp ties to political engagements. Moneyed Winston FC Guest played tennis and lounged at the famous Palm Beach landmark The Breakers Hotel in his all-white shirt, sweater and trousers ensemble. The American bluebloods Biddles, Dukes and Drexels made glamorous social rounds in navy blazers and crisp white flannel pants. Lilly Pulitzer, a designer and socialite out of Palm Beach, became the outfitter of the cool preppy female set, churning out sunny sleeveless shift dresses, pants, tunics and swimsuits.

Preppy crossed over to Europe as well: on casual jaunts the Duke and Duchess of Windsor were often photographed in an elegant preppy wardrobe. Englishman and advertising executive David Ogilvy, the prototypical Mad Men male, was a hardcore-preppy suit kind of man. Even Rene Lacoste, the French tennis player, got bitten by the preppy bug and became a preppy poster boy with his croc-logoed lightweight cotton piqué knit tennis shirt — his polo became a staple of Ivy Leaguers and the country club set after World War II in America.

Women finally own the Ivy style: The first-ever button-down shirt in pink for women by Brooks Brothers in a 1949 Vogue, with the gold charm bracelet, an Ivy style must-have.

Ivy Style Makeover

Preppy remained refined and exclusive to WASPs well into the 1960s but transformed into an inclusive, multi-racial, multi-ethnic, multi-religious, pan-gender, meritocratic way of dressing in the succeeding decade. The era of open admissions welcoming urban ethnic minorities into Ivy League schools led to this change and the subsequent diffusion of the preppy style. The traditional and straight-up preppy was tweaked with a twist and preppy became hip.

The late ’70s saw the rise of Ralph Lauren, a former Brooks Brothers salesman, as a premier preppy designer. He started a company of fine men’s clothing and sportswear called Polo, after the world’s most elegant sport, which not only redefined the preppy look but inspired a whole new lifestyle. He made the fabrics more luxurious, colors more lush and sweater cables thicker; he created an aspirational preppy lifestyle that encompassed ideal houses with manicured lawns, perfectly coiffed wives and well-behaved children complete with pet dogs. From clothing he expanded his brand to include home furnishings and accessories — even wallpaper and paint. Ralph Lauren successfully built a fashion empire around the Ivy style.

The 1980s ushered in a new generation of Ivy Leaguers called “yuppies,” flush with money and engaged in high-profile professions like investment banking and stock brokering. They spent money on a bolder and more vivid take on the classic American style, as epitomized by the 1980s cult classic movie Wall Street starring Michael Douglas. In 1984, another American designer, Tommy Hilfiger, emerged from anonymity to become a driving force in the preppy fashion industry with his signature red, white and blue yuppie clothing.

Palm Beach fashion: Designer Lilly Pulitzer brings her bright, sun-drenched cotton dresses to Ivy-style heights, 1968.

For the rest of the 20th century, preppy took a dominated the fashion scene, minimalist became the trend and dressing down became the new cool.

Preppy style, 21st century

If the late ’90s signified fashion restraint, the beginning of the 21st century was the complete opposite. Expensive designer shoes and bags became the fashion norm, “bling” became a fashion byword and “more is more” became the fashion mantra.

All this changed in the latter half of 2008, though, in part as a protest to the dominance and influence of trashy pop culture on reality TV. Established brands and new designers alike brought back a hipper, more upscale take on the preppy style with a twist of sexiness and shape — preppy became more embellished and less androgynous. J. Crew developed an uncomplicated, price-conscious alternative to the more expensive preppy brands and built its mail-order catalogue business into a preppy fashion behemoth.

Abercombie & Fitch, the great American heritage brand since 1892 that had been outfitting professional sportsmen and women like Amelia Earhart, re-emerged under the ownership of Limited Brands and the stewardship of Michael Jeffries to become the preppy lifestyle brand of choice with their cool marketing campaigns geared towards the upscale American collegiate audience with a fondness for the great outdoors.

Brooks Brothers teamed with Thom Browne to develop a preppy line called Black Fleece. Gant, another heritage brand, collaborated with Michael Bastian for a relaxed and sophisticated lacrosse stick-logoed take on the preppy polo shirt. LL Bean, for its centennial celebration, is mining its archives for a more modern version of its all-time classics.

When preppy turned yuppie: Michael Douglas brings the sharper version of preppy to the boardroom in this ensemble by master tailor Allan Flusser in Wall Street, 1987.

Ralph Lauren continues to dominate the preppy world of fashion with his luxurious advertising campaigns and plush lifestyle retail stores. Tommy Hilfiger, a music lover, capitalizes on his associations with famous musicians like Lenny Kravitz, Britney Spears and Snoop Dogg to market his 21st-century version of preppy.

While many trends have come and gone, the future of preppy is secure. Its elegant, classic and timeless American-to-the-core appeal from more than a century ago remains stalwart, proving that preppy style is undoubtedly America’s most important legacy to the world of fashion.

Preppy: Cultivating Ivy Style takes us on a colorful, historical ride from the insular, elite and quite snobbish appeal of Ivy style in the 1920s to its 21st-century incarnation. The book is divided into seven chapters and contains never-before-published photographs and vintage advertisements that depict Ivy style in all its fashion glory. Lilly Pulitzer provides the foreword to the book.