Elle Macpherson in a Dior dress, a Buccellati cuff, a Cartier ring, and Christian Louboutin booties.

Photographed by Max Farago. Page 462

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The first thing you notice about Tommy Hilfiger is that, at 59, he still has a vaguely mischievous, youthful quality—the knowing wink, the faintly ironic grin, the easygoing charisma that works quickly and well. It’s the same demeanor, one imagines, that contributed to his success some 41 years ago as an enterprising Elmira, New York, teen, selling bell-bottoms from his VW bug .

For Hilfiger, the Great American Wardrobe is a wearable riposte to the Great American Songbook:

a shared cultural heritage that continues to evolve and accrue layers of meaning the more it is reinterpreted. He knew it even then: Those bell-bottoms were bigger than fashion. They were a symbol of what it was like to be young and American in a time when the innocence and simplicity of a hierarchical all-American life was coming apart at the seams. It was an era full of possibilities, and young Hilfiger was just the guy to grasp them. “Up until then, it was all about Elvis, Motown, and musicians dressing in suits and ties,” Hilfiger says. “Then there was a fashion revolution that affected everyone’s lives.”

Hilfiger’s business outgrew his car and spilled into his first shop, People’s Place, which spawned nine more throughout upstate New York. But youthful idealism did not equip him for the realities of business. Going bankrupt in 1977 , he says, was a turning point. “I decided I should really learn how to manage the business and how to keep my finger on the pulse,” he says. Not that he was headed to grad school. “I learned from life experience.”

In the early ’80s, he met Mohan Murjani, the investor behind Gloria Vanderbilt who wanted to launch a menswear brand with a man’s name. Hilfiger, incredible as it sounds now, suggested short-ening his own surname to Hill. No way, Murjani said. “Hilfiger” might be hard for people to pronounce at first, but it would be equally hard to forget.

Soon enough, an inspired bit of guerilla marketing would put that name on the fashion map. In 1985, George Lois, the visionary art director of Esquire, concocted a cheeky, fill-in-the-blank Times Square billboard that read THE 4 GREAT AMERICAN DESIGNERS FOR MEN ARE… with each designer (Ralph Lauren, Perry Ellis, Calvin Klein, and Tommy Hilfiger) identified only by their initials . According to reports at the time, the reigning three musketeers of American menswear weren’t amused by the stunt. But the truth was, while Ralph was on the ranch or at a Gatsby party, and Calvin was sensationalizing denim and schmoozing at Studio 54, the mys-terious T. H. was beginning to peddle his own slice of the American dream, with himself as a sort of Warhol figure (down to the mop of hair) inviting us to consider the quotidian classics anew.

By the ’90s, Tommy Hilfiger stores were sprouting up across the country, perfectly timed to another revolution, one Hilfiger calls the “casualization of the world.” It wasn’t exactly the full-throated protest of the Easy Rider years but just as fundamental in its way: The loosening of strict dress codes that divided young from old, work from weekend, made way for what he calls a “preppy all-

American sportswear brand, youthful in spirit but still affordable and acceptable,” e.g., striped polos, khakis, and schoolboy jackets that were literal riffs on private-school staples.

And then came hip-hop.Hilfiger’s side step into that world, with its oversize, urban take

on polo shirts, denim, and logos, was groundbreaking for its genu-ine street cred—but occurred by accident. After Hilfiger’s younger brother, a rock musician, introduced him to his rapper friends, the designer began tweaking his clothes to their tastes, more as a favor than business strategy. Then in March 1994, he was anointed: Snoop Dogg performed on Saturday Night Live wearing a red, white, and blue Hilfiger rugby. The look sold out the next day .

A lifelong fan of pop music and pop culture, Hilfiger has over the years featured everyone from David Bowie and Lenny Kravitz to Britney Spears and Beyoncé in his ads. He has sponsored tours for Sheryl Crow, Pete Townshend, and the Rolling Stones (his house on Mustique is next door to that of good friend Mick Jag-ger). But it was hip-hop that made him famous. With that commu-nity behind him, nobody needed to ask who T. H. was. In 1995, he cemented his stature with a CFDA Menswear Designer of the Year award; he launched women’s wear the following year.

But by 2000, the year Hilfiger’s company went public, Sean Combs and Russell Simmons—friends who’d once turned to him for business advice—were undercutting his market with their own labels. As suddenly as hip-hop embraced him, it turned away. “Our urban run was great,” he says, “but having to shift our focus back to our classic heritage was one of the best things that ever happened.”

After a two-year hiatus from the runway, he returned to New York Fashion Week in 2007 with an edgier, more fashion-savvy take on what he’s always described as “classic, American cool” (wit-ness fall’s thigh-high duck boots, cropped camel kilts, and ’60s pea-coats). Hilfiger’s masterstroke, however, has been marketing Americana prep overseas; today, 80 percent of Hilfiger stores are located abroad , and the brand has never been more successful. In March, it was sold by private equity firm Apax Partners (which ac-quired it in 2006) to apparel magnate Phillips-Van Heusen for about $3 billion.

Ultimately, America—or Hilfiger’s idea of it—came through for him. In that somewhat mythological place, the seemingly contra-dictory worlds of rock ’n’ roll and Norman Rockwell meet; the “honest masculinity” of a gas-station attendant is as valued as the “simple, clean, and classic” chic of Grace Kelly—and his red, white, and blue logo is as much a part of the international sema-phore as the ornate calligraphy on a bottle of Coca Cola, or the red tab on a pair of Levi’s.

Tommy Hilfiger 25th-Anniversary pieces. From left: Plaid wool stadium coat, $598, plaid dress, $298, wool scarf, $198, leather belt, $128, watch, $85, python and leather clutch, $298, tights, leather and rubber boots, $298, denim shirt, $88, silk and wool pants, $248, leather belt, $128, leather boots, $298, all, Tommy Hilfig er, at Tommy Hilfiger, NYC, call 212-223-1824. Mr. Hilfiger wears his own clothes. For details, see Shopping Guide.

P H O T O G R A P H E D B Y pierre bailly

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FROM OUTFITTING ’60S HIPPIES IN BELL-BOTTOMS TO UNIFORMING EUROPEANS IN STANDARD PREP—PLUS A $3 BILLION BUYOUT THIS PAST SPRING—TOMMY HILFIGER IS CELEBRATING HIS 25 YEARS BY BRINGING HIS SMART, CHIC STYLE HOME TO STAY. BY NICK FOULKES

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INSIDERPagE 356 Carita Fluide de Beauté 14, $69, caritadirect .com. Elizabeth Arden Eight Hour Cream, $17, elizabetharden.com. La Roche-Posay Physiological Eye Make-Up Remover, $19, laroche-posay .us.com. Laura Mercier Eye Liner in Bleu Marine, $22, Secret Camouflage, $28, and Sheer Lip Colour in Baby Lips, $20, all at lauramercier.com.

aN Eau of ouR owNPagE 360 “25” Editions de Parfums Frederic Malle, $150, 212-249-7941.

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zoNE DEfENSEPagE 368 Bulgari Source Defense Serum, $190, bergdorfgoodman.com. Clinique Repairwear Laser Focus Wrinkle & UV Damage Corrector, $45, clinique.com. Dr. Dennis Gross Extra Strength Alpha Beta Peel, $85, mdskincare.com. Elemis Pro-Collagen Body Serum, $86, timetospa.com. Elizabeth Arden Ceramide Plump Perfect Ultra All Night Repair and Moisture Cream, $62, elizabetharden.com. Estée Lauder Advanced Night Repair Synchronized Recovery Complex, $48, esteelauder.com. Garnier Fructis Style Sleek & Shine Blow Dry Perfector 2-Step Smoothing Kit, $12, at drugstores. Kate Somerville ExfoliKate Body, $65, katesomerville.com. L’Oréal Paris Visible Life Serum Absolute, $15, lorealparis.com. Oribe Hair Care Dry Texturizing Spray, $39, oribe .com. Pantene Pro-V Restore Beautiful Lengths Shine Enhance Shampoo, $5, at drugstores. Redken Time Reset At Home Porosity Filler Kit, $20, redken.com for salons. StriVectin-SD Intensive Concentration for Stretch Marks and Wrinkles, $135, strivectin.com. Super by Dr. Nicholas Perricone Supermodel Legs, $30, at Sephora.

IT LISTPagE 388 Clinique Great Lips, Great Cause Limited-Edition lip trio key ring, $16, at Macy’s. Darphin Paris Intral Soothing Cream, $70, darphin.com. Elizabeth Arden Pretty Eau de Parfum Spray, $52, shop.elizabeth arden.com. Estée Lauder Pink Ribbon Collection lipsticks, $25, Pink Ribbon Collection Jeweled Pink Ribbon Pin, $13, all at esteelauder.com. Kim Kardashian Rollerball Fragrance, $16, sephora.com. OPI Nail Lacquer Pink of Hearts 2010, $9, ulta.com. Red Flower Moisturizing Body Lotion in Japanese Peony, $24, redflower.com.

ThE agINg of INNocENcEPagE 374 Chanel No. 5 Eau de Parfum spray, $62, chanel.com. Mason Pearson Boar Bristle Hairbrush, $170, drugstore.com. Maybelline New York Great Lash Mascara, $5, drugstore.com.

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L’Oréal Elnett, $15, lorealparisusa.com. Mason Pearson Boar Bristle Hairbrush, $170, drugstore.com. Nars Orgasm Blush, $26, narscosmetics.com. Rene Furterer Naturia Dry Shampoo, $34, sephora.com. Shu Uemura Eyelash Curler, $19, shuuemura-usa.com. YSL Touche Eclat Highlighter, $40, yslbeautyus.com.

foREvER 25PagE 364 Dr. Brandt Time Arrest Crème de Luxe, $200, drbrandtskincare.com. Olay Pro-X Age Repair Lotion SPF 30, $30, at drugstores. SK-II Skin Signature Melting Rich Cream , $250, sk-ii.com.

ELLE BEAUTY gUidE

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