TO UNDERSTAND SOMETHING DEEP and true and deceptive about the American Dream, picture a young Tommy Hilfiger racing frantically toward downtown Elmira, New York, on June 22, 1972, in the hours before Hurricane Agnes hits. He has a store, and a future, to save.
Hilfiger, on that day, is just about the hippest guy in Elmira, the small, working class town where he grew up with his eight brothers and sisters. He’s 21, has stylishly long hair, is wearing the right early Seventies clothes, and with his buddy Larry Stemerman is the founder and owner of People’s Place, the only store for leagues in any direction that carries counterculture-inspired clothes for the young and hip. At night the store, which occupies the basement of a building downtown, also happens to be a good place to party. So Hilfiger and Stemerman are having a great deal of fun – girls, drugs, rock n’ roll – while also making a good deal of money.
Hilfiger has just returned from a long trip to London, where he was scouting out new fashions for the store. It had been a good trip. He’d soaked in that particular brand of rock-meets-fashion cool that London had perfected. He’d found an amazing brand of jeans, Made in Heaven, that he was planning to import and distribute in the States. He’d worked for a few weeks at a boutique on Kings Road, one of the hubs of Sixties fashion, to get a sense of how the UK did retail. He had also gotten a useful shock to his still fairly parochial consciousness.
‘After weeks on Kings Road,’ Hilfiger writes in his recent memoir, ‘my store seemed so provincial now, so behind the times. I wanted real excitement. I began looking for something else to do. I dreamed of creating my own brand.’
All this excitement, ambition and frustration are swirling around in Hilfiger’s head, that day in June, when he and Stemerman notice that the Chemung River, which runs through the centre of Elmira, is getting unusually high. If it keeps raining, it’s going to flood.
Hilfiger and Stemerman get back to town, and with the help of a ‘brigade of hippies, high school kids, college girls,’ and most of the Hilfiger clan, are able move their clothes up from their basement store to the top floor of the building. By the next morning much of the town is under a few feet of water.
It’s a disaster for Elmira and the surrounding areas. Homes and stores are flooded out. Bridges are washed away. 18 people die in the nearby town of Corning.
For People’s Place, it’s an opportunity. For Hilfiger, it’s one of those moments when his American dream advances palpably closer to reality.
‘It dawned on us,’ Hilfiger writes. ‘If every store in the entire valley was wiped out, there were no more clothes in Elmira. Except ours.’
Hilfiger and Stemerman open their doors to the grateful, and desperate, people of Elmira. Within a few months their style is mainstream Elmira.
‘We saw dads in tie-dye and little old ladies wearing bell-bottoms,’ he writes.
When Hilfiger had started People’s Place in 1969, he wasn’t the only 18-year-old in America who knew what the fashions were. But he may have been the only one who encountered the new style and then immediately started a successful business selling it to his peers in the provinces, and then to their parents and grandparents when opportunity beckoned. His ambition was exceptional, as was his efficacy.
In the aftermath of the flood, People’s Place expanded, moving up from the basement to occupy the first and second floors as well, adding new lines and goods. They did hair on the second floor, and sold records in the basement. Tommy and Larry got into promoting rock concerts, and also joined the Chamber of Commerce. Hilfiger kept the inventory fresh, with regular scouting trips to London and New York, Los Angeles and Paris, ‘anywhere people were having fun.’ They brought some of Hilfiger’s brothers and sisters into the business, and opened People’s Place stores in Corning, Cortland and Ithaca.
Stemerman was a sharp businessman, but it was Hilfiger’s eye that fuelled the growing empire. He was always looking, whether at a trade show a rock concert or Studio 54, assessing not just what the cool kids were wearing, but guessing what they might be wearing next, and travelling in as many circles as possible to put himself in the way of inspiration whenever and wherever it might appear.
‘I was like a sponge,’ he writes. ‘Anytime I went to a factory or store, I wanted to learn more, more, more, because I knew this was not the last stop on the train.’
Soon he began developing some of his own designs, and looking for someone to produce them, but if Hilfiger had a genius, it was less about saying something radically or interestingly new with clothing than about understanding how to curate, translate and market niche aesthetics for a broader audience. His enthusiasm for countercultural fashion, it soon became clear, was opportunistic rather than philosophical. His was a fundamentally pop genius, dependent on his ability to give the mainstream just as much edge and titillation and fantasy as it could handle, but no more. Dependent as well – fatefully, as it would turn out – on forces beyond his control, on the whims of the market, history, and the zeitgeist.
When he finally did launch his own line, in 1984, the brilliance wasn’t in the look, which was a variation of other mass market prepster brands like Ralph Lauren and Lacoste, but in the price point, the marketing and the business plan. There was room in the market, Hilfiger intuited, for preppy clothes that were expensive but not so expensive. He splashed his nautically-inspired logo, and his name, on the clothes in ways that might be aversive to actual members of the preppy elite but were seductive to the aspirational classes beneath them, people who didn’t come from money but now, in the wealth-embracing air of the Eighties, wanted to look like they did and wanted to let you know that they could afford to look that way. He innovated in the development of his supply and production cycle, finding ways to speed up the process so that new looks could make it into the store faster. He balanced the churn of new looks, for consumers who wanted what was new, with a more stable offering of basics, for consumers who were less adventurous. He was intensely alert and responsive to opportunity.
Throughout the Eighties, thanks in large part to Hilfiger’s design and business instincts, sales and brand awareness grew quickly. He had made it. But it would take another serendipitous confluence of culture, capitalism and opportunity for the brand to ascend to the kind of top-tier market presence Hilfiger really wanted.
Good fortune arrived in 1991, one early morning when he and his brother Andy were at the airport in New York, just back from a trip to visit suppliers in Hong Kong. They were waiting at the baggage claim when Andy noticed the rapper Grand Puba, and his fellow members of Brand Nubian, standing near them. They were wearing a whole lot of Hilfiger.
The rest of the story is fashion business legend. Andy and Tommy introduced themselves, and invited the fellas to the Hilfiger showroom in Manhattan to see the new stuff and take what they wanted.
‘Two days later, the whole crew came down, and we gave them clothes. They were happy, and we were happy. They started wearing our line in their videos, and we saw a groundswell of Tommy Hilfiger awareness and sales to the urban customer. All of a sudden, hip-hop stylists and artists all wanted Tommy Hilfiger, and Andy was in charge of product placement. “You’re going to do a video? Come on up!”‘
Hilfiger, in what was perhaps the last great spike of his particular genius, recognised a few things. Times had changed, and his brand – fortuitously, accidentally – was already speaking to the ascendant hip-hop culture, with its half-ironic but half utterly earnest embrace of the aspirational WASP aesthetic (before Hilfiger, the hip-hop-WASP brand had been Polo). That affinity could be refined and amplified from the company’s direction, with designs that took some more explicit cues from hip-hop, and marketing and promotional efforts that made sure their clothes were on the right trend-setters. And if the company handled it right, they could take advantage of that connection without alienating their base of middle American white consumers.
Over the next few years, the logos and Hilfiger name got bigger and louder, the fit got baggier and the company expanded enormously. It sold not just to the black folks who were influenced by hip-hop culture but to the white folks who were taking their style cues from the black folks, and still, somehow, to all the millions of mostly white folks people who didn’t care much at all about hip-hop but knew, vaguely, that Hilfiger was cool. By the end of the Nineties Tommy Hilfiger was one of the biggest fashion labels in the country. It was the grand success of which Tommy had always dreamed.
The Tommy Hilfiger story, to this point, is a compelling one, in the way that entrepreneurial success stories often are. He wasn’t one of the great artists of the fashion world, but he had built a relevant brand, and had some meaningful influence on American culture. He genuinely saw possibility, in cuts and fabrics and visual vocabularies, that no designer had seen before, or that no one had been able to scale up to the mass market before, and over many years he acquired the business skill and experience to realise those ideas in the form of actual clothing that could be sold in stores around the world.
Fascinating too – and this is what elevates his significance beyond the entrepreneurial into the realm of American Pop – was the utter earnestness that he brought to his empire building, a sincere belief that the vision of American life he was selling, through his brand and clothes, was inspiring to his consumers. It was an earnestness that shapers of American pop dreams like Hilfiger often seem to have, maybe have to have, in order to speak to our fantasies so profitably.
‘I’ve always loved the look and feel of yachting and sailing and being on the sea,’ Hilfiger writes in his memoir, reflecting on how he first conceptualised his brand. ‘It conjures places in the world infused with wealth, warmth, romance, excitement, inspiration and aspiration: Newport, Nantucket, Portofino, Saint-Tropez. Just as in my dreams as a boy, being on the water is all about escapism. It embodies class. I think of Jack and Jackie Kennedy. The good life is something everyone wants.’
It’s possible to take this as just promotional copy, manufactured by a team of Hilfiger corporate flacks to reinforce the brand, but it doesn’t read that way. The earnestness, almost innocence, reads as genuine, and as psychologically consistent. And taking it on its own terms makes sense of the rather sad final third of his memoir, Tommy Hilfiger: American Dreamer, and also of the last 15 years of the life and career of Tommy Hilfiger, actual American person.
The thread is lost. The syntax goes flabby. The anecdotes go slack. It becomes a lifeless story of business transactions and celebrity ‘friendships’ and partnerships. The company goes public. It goes private. It’s acquired by another company. Top executives leave and other top executives come in. There’s a crash. There’s a recovery. Tommy restructures his ownership stake, and then restructures again. They make a fragrance for Jennifer Lopez. He becomes buddies with Tommy Mottola, who is just wonderful, and collaborates with Mottola’s young new wife, singer Thalia. She too is fresh and wonderful. He meets lots of other incredibly wonderful and talented people, who are so wonderful. He feels lucky to know them. And so on.
It lacks the emotional and narrative coherence of everything that came before, and is unpersuasive. More persuasive is the story that we can stitch together from the subtext of the book, and from Google, about what happened to Hilfiger in the late 1990s and early 2000s. Things fell apart. A number of his longtime partners and investors left the company. He got divorced from his wife Susie, who had been an anchor for him as he built his empire. Hip-hop moved on to labels, like Rocawear and Sean John, that came more directly out of the culture, and the Hilfiger label lost some of its heat (and profits). At around the same time, middle America decided that it had had enough of hip hop-ified fashion, and moved on from Tommy Hilfiger. More profits were lost. It was a rough few years.
Hilfiger remarried in 2008, and the company’s financial fortunes recovered, but somewhere along the way he lost something more essential even than his wife or his old comrades-in-arms. He lost, or gave up, or was stripped of, his place at the entrepreneurial heart of the company, where his talent, ambition and savvy were driving it forward. Maybe he’d lost his eye. Maybe he didn’t trust it anymore. Maybe he’d lost his drive. Or maybe the business had simply gotten beyond him. Whatever the reason, he wasn’t chief dreamer of the dream factory anymore.
At the end of the book, he admits as much. After the company was acquired in 2010 by Phillips-Van Heusen, his figurehead status was formalised with his designation as brand ambassador.
‘I am no longer sketching out the styles, picking the colours and buttons, adding the stripes,’ he writes toward the end of the book. ‘I miss the days when I could touch everything, but because of the size of Tommy Hilfiger … it would be impossible for me to participate in every design meeting. I have basically let go, and I am somewhat relieved not to have the pressure on a day-to-day basis. … I couldn’t be in a better position. And I do the fun stuff! The fashion shows. Flying to Shanghai to open a store. Determining the direction of our advertising. Collaborating with stars like Gigi Hadid, Zooey Deschanel and Rafael Nadal to keep the brand fresh.’
This isn’t an intrinsically tragic place to end up. It’s where many great entrepreneurs and business visionaries land, after building their empires, still involved but no longer at the white hot centre of the action. It’s where many successful fashion entrepreneurs, in particular, end up, settling into profitable conservatism after a brief, golden efflorescence of originality and influence. Hilfiger is now 65, an age when most men or women are past the point when they have the energy, or would want to expend the energy, to manage a multinational corporation. It’s easy to imagine many ways that someone in his position, with his wealth and talent and influence, might live a meaningful and satisfying next act.
To genuinely do that, though, Hilfiger would have to come to some kind of terms with the absence at the centre of the American dream, or at least the grandiose version of the dream to which he has subscribed. The promised rewards – cutting the ribbon on a new store in Shanghai, hanging with Zooey Deschanel, befriending Tommy Mottola, and summering in St. Tropez – sound genuinely fun (maybe not Mottola, but the rest of it). They don’t bring contentment or satisfaction, though. It’s the work you do to get the fun stuff, not the fun stuff itself, that creates meaning. Or if you’re a different kind of person the meaning comes from family, friends, art, God, or good works. For Hilfiger it has clearly always been the work, and the fantasy of what it can bring.
For Hilfiger to make something as striking of his last years as he made of his first 50, he would have to get back to work. He’d have to bull his way back to the heart of the Hilfiger brand, and radically revitalise it, restoring coherence, energy and brashness to a brand that no longer knows who or what it is, aside from being a highly profitable but culturally uninteresting younger brother to J. Crew and Ralph Lauren. No more vague and backwards-looking collaborations (nautical-themed Americana with Gigi Hadid one day, Nineties hip-hop with Urban Outfitters the next). No more well-funded but mostly directionless publicity stunts (carnival-themed fashion shows, crowdsourced collections1 ). He’d have to burrow his way into the living current of the American dream, as he once did, and write a new kind of pop song in clothes.
I have no idea what that would look like. The straight WASP fantasy isn’t in right now. But it runs too deep in our culture, and our collective idea of what success, wealth and status look like, to remain out of fashion forever. It will be reinterpreted and revived, almost certainly by some man or woman from the provinces, fired by a dream, who has set out to conquer the world through stylish clothes.
Probably not by Hilfiger, who too often seems to be subsisting, now, on a backward looking fantasy. He seems a kind of ghostly after-echo of that stylish, ambitious young man on the top of a hill in Elmira, now living in the dream of his own label, with nowhere to run and no flood to outwit and exploit.
‘I am honored to still be involved in the growth of the Tommy Hilfiger brand,’ he writes, in the last, lonely paragraph of the book. ‘It is my creation. It’s my baby. I couldn’t be happier that the DNA is intact, and the dream I conceived all those years ago, with no money in my pocket and an armful of sketches, is still alive. As a boy in school, dreaming, I thought I had big things in store, but I didn’t know how my dreams would ever come true. I hoped and prayed that they would. I’m grateful to be a dreamer, and always will be.’
Daniel Oppenheimer is a writer and short documentary filmmaker in Austin, Texas. Exit Right, his first book, was published in 2016.