By Steven Stolman | October 26, 2014 | Lifestyle
Nearly 35 years after the publication of The Official Preppy Handbook, Windy City residents’ penchant for plaid is alive and well.
Christopher Makepeace in 1980’s Chicago-set My Bodyguard.
“Please watch your profanity, preppy.”
“Why do you think I went to prep school?”
“You look stupid and rich.”
And so went the exchange between Ali MacGraw and Ryan O’Neal as star-crossed college students (Radcliffe/Harvard) in the 1970 tearjerker Love Story. And while the term “preppy” was certainly nothing new, that line brought it into the limelight. Remember, stylistically, the late ’60s were about as far away from preppy as punk or goth. Pant legs were elephantine to accommodate platform shoes, shirts were cut from clingy fabrics like Qiana that demanded near-anorexia, and hair was long, frizzed, or feathered. This massive attack on taste was a direct response to the repressed, buttoned-up ’50s and early ’60s, the turbulence of the race and gender wars, and, more than anything else, drugs. For a while there, it seemed as if everybody had just stepped out of a Peter Max poster.
“We wore our own clothes for the unscripted scenes,” remembers MacGraw. “Most of mine came from The Villager.” (For those under 50, The Villager was a leading women’s sportswear company founded by Max Raab and famous for its Ivy League styling.) MacGraw’s wardrobe of peacoats, turtlenecks, kilts, tights, and long scarves became the uniform of preppy girls in cold climates everywhere, along with O’Neal’s shearling coat, Shetland sweaters, and pinwale cords.
Ryan O’Neal and Ali MacGraw in the 1970 movie Love Story, which popularized the term preppy, along with its collegiate style.
Though it was filmed 45 years ago and took place in Cambridge and its environs in Massachusetts, the preppy sartorial style of Love Story is alive and well in Chicago today, as Chicago’s core prepsters will attest. Just look at folks like local designer Brion Judge, whose carefully considered ensembles of Tattersall, tweed, and rep stripes outdo the latest rigs from the Polo empire. John Cialone—another Chicago designer who once ran Stubbs & Wootton, the purveyor of posh velvet slippers—dresses similarly. “Classic attire,” he says of his look. “Never stylish, but also never out of style,” favoring items that are “tailored, handmade, monogrammed.” Hipster stores like Haberdash for men have opened up a wide array of options to fill the closets of Chicago’s preppiest preps. So have Tiffany, Gucci, Prada, Burberry, and other purveyors of deluxe dressing. J. Crew and Lillie Alexander, the Lake Forest boutique that continues to be Lilly Pulitzer central, round out the mix for Chicagoans’ options for weekend wear. Julie Christopher, a regular fixture on the preppy social scene, endorses Hermès as the quintessential accessory brand of her set, citing “a double wrap watch and a haphazard stack of colorful enamel bracelets” as the encoded essentials.
Ironically, the preppy lifestyle has been depicted most accurately through several films set in Chicago. My Bodyguard and Risky Business both featured characters who would undoubtedly grow up into denizens of Chicago’s Casino Club. But it was the extraordinary Ordinary People, director Robert Redford’s tale of angst set in Lake Forest, that showcased the Midwestern preppy to a T. Donald Sutherland’s golfy, LaSalle Street lawyer was spot on (one could easily envision him on one of the Racquet Club’s squash courts); Mary Tyler Moore was sublime in her tailored sportswear and subtle jewelry; and Timothy Hutton and Elizabeth McGovern—today Downton Abbey’s Cora Crawley—were the epitome of the preppy kids that would ultimately become residents of Willard, Northwestern University’s deluxe dorm.
William Spencer Jennings sports a vintage summer look.
Granted, Chicago prep style is most certainly not the same as its East Coast counterpart. Says Chris Berre of new lifestyle brand Artfully Disheveled, known for its spirited neckties and pocket squares, “In Chicago, prep style has a Midwestern touch: a little more casual and often mixed and matched with hipster pieces.” Adds Lisa Birnbach (author of the groundbreaking Official Preppy Handbook, which nailed every aspect of preppydom so perfectly that only she was qualified to write its 2010 sequel True Prep: It’s a Whole New Old World), “In the winter, the Chicago preppy can layer with impunity,” citing “an attitude of pleasurable expectation that is less jaded than [his or her] East Coast cousins.”
The modern-day Chicago preppy is certainly less formulaic than that of the past. Apparel (“the rig”) is far more relaxed and eclectic, with a very decided nonchalance that is, at once, more authentic than the strict sartorial guidelines of the 1970s, ’80s, and even ’90s. The appearance of global luxury brands in and around the Magnificent Mile, along with the access of the Internet, has opened up the ability for Windy City preps to dress as chicly as their counterparts in New York, DC, or London, for that matter. And then there’s Ralph, whose largest store in the world has occupied the corner of Michigan and Chicago Avenues since 1999.
A look from Michael Bastian; New England favorite Vineyard Vines has recently arrived in Chicago.
Preppy is also no longer just a look for the country-club set. Designer, author, and expert on preppy style Jeffrey Banks explains, “The difference with today’s prep scene is that it is much more inclusive than the ‘old boys’ culture of previous years. You don’t have to have belonged to a fraternity or have gone to Amherst to wear traditional Ivy League clothing. For many young men today, preppy is just one more clothing option to wear and enjoy without necessarily having the legacy family tieins that used to be associated with preppy dressing.” Adds Simon Doonan, creative ambassador for Barneys New York, “Today’s preppy guy has reinvented the old-school Ivy-League formula. He has a dash of hedonism. The clothes are more tailored. The look is definitely sexier. Think Alain Delon, or Michael Caine.”
For prepsters this fall, a plethora of styles run the gamut from nonchalant to self-consciously stylish. Ralph Lauren’s men’s Purple Label collection mixes a fitted Royal Stewart tartan jacket with faded jeans rolled just so to reveal exactly the right amount of yellow cashmere sock jammed into priceless loafers. In other words, it’s all about high-low and dressy-casual—the kind of fashion juxtapositions made famous by prep icon C.Z. Guest, who paired couture taffeta ball skirts with a T-shirt while Sharon Stone was still in diapers. Arthur Wayne, the voice of ground-zero prep retailer Brooks Brothers, singles out the ultra-sophisticated Black Fleece collection designed by Thom Browne, who plumbs the firm’s 200-year-old archives and then applies a modern spin. “This season, expect to see a mix of pale pink and gray plaids for men and women, plus Browne’s signature gray flannel.” If any trend has emerged as a preppy front-runner this time around, it’s a studied eclecticism that’s always in style.
The Yacht Club remains one of Chicago's old bastions.
So why has the preppy look endured? Answers Perry Ellis creative director Michael Maccari, “Because it is timeless. Guys understand clean, good quality—pieces that work back into their wardrobes—and to me those are at the heart of preppy.” Much-loved menswear designer Michael Bastian, who typically pairs Nantucket red trousers with a classic tuxedo jacket for his own black-tie turnout, echoes that sentiment. “Preppy is really the American guy’s default setting,” he says, warning that “it’s when you overthink it that it gets all precious.” His fall 2014 must-have? “A Shetland blazer.” Jeff Halmos, who codesigns the heritage brand Haspel with Sam Shipley, says, “The term itself is really just a collegiate way of explaining classic American style. It’s an enduring look that gets passed down from generation to generation.”
Women have always had an easier time with the preppy look, as Talbots had already embarked on its crawl from Hingham, Massachusetts, to malls across America. But ground zero was definitely the Lake Forest Shop, founded in 1922 and now run by the granddaughter of the original owner, Ellen Stirling. It even had its own Pappagallo shop within the store, providing thousands of preppy women with their “Blossom” flats, the precursor to the Tory Burch “Reva” ballerina. Lilly Pulitzer’s rambunctiously printed clothing was only marginally available in a tiny eponymous boutique in the Deer Path Inn (managed by one of her buddies, Mari McCormick, who also owned the inn), but companies like Jax, Jamison, and Carroll Reed, along with trips to Trimingham’s in Bermuda, helped round out a proper preppy wardrobe.
Le Pain Quotidien in Lincoln Park is another Chicagoland mecca for prepsters.
Next to dressing up, preppies love a good time out on the town. After outgrowing college bars (do they ever, really?) the natural progression is to places that sport a decidedly retro, clubby feel, and preferably a real club. In the pecking order of answers to “whereyawannago?” the Casino, Saddle and Cycle, or the aforementioned Racquet Club top the list. When the Pump Room pumped its last drop of glamour and Cricket’s—the quintessential prep hangout in the Tremont hotel—was converted into a Ditka’s Steakhouse, RL took over as the purveyor of swank, and still manages to pack them in with dishes like chicken hash and Dover sole. New to the scene, the two-year-old Tortoise Club is clearly going after RL’s lunch crowd, with preppy favorites like Cobb salad and, of course, that classic sole.
Prep style seems to cycle back to the front of the line every decade or so. Popped collars on polo shirts have made a comeback, as have circle pins and headbands. Brightly colored trousers seem to be everywhere these days, courtesy of companies like Vineyard Vines and Bonobos, as are Topsiders and wing tips. And from outward appearances, the East Coast preppy and the Midwestern preppy basically look the same. But it’s the intrinsic tenets of a Midwestern life—a mix of no-nonsense values, lack of pretentions, and aw-shucks charm—that will always delineate the preps in these parts as decidedly top-drawer.
photography courtesy of everett collection