“Tommy Hilfiger was so important growing up in Chicago, I used to go to the local mall and steal his clothes,” admitted celebrity stylist Law Roach, going off script at the British Fashion Awards on Monday night as he took to the stage alongside Kris Jenner to present Hilfiger with this year’s Outstanding Achievement Award, in celebration of his four-decades-long contribution to fashion. “I was willing to risk it all for a pair of Tommy overalls!”
Roach wasn’t the only teen obsessed. As he took the mic to accept the award, Hilfiger, oozing all-American polish in a royal blue velvet suit, said that in the last conversation he’d had with the late fashion designer Virgil Abloh, who passed away on Sunday following a cancer battle, the Off-White label founder told him that he didn’t do a day at high school in Chicago without wearing Hilfiger’s clothes.
“We were first to do streetwear,” says the 70-year-old, when we meet in his Knightsbridge offices just hours before he hits the British Fashion Awards red carpet with shoe designer Dee Ocleppo, his wife of 13 years. Hilfiger looks quintessentially preppy and polished in a blue suit, white shirt, navy jumper and brown loafers. “We did streetwear in the Eighties before other brands…. when I started doing big logos, nobody had big logos,” he says. “Even Ralph Lauren just had the little horse. The big Polo came later.”
An upstate New Yorker with no formal design training, Hilfiger launched his first fashion business, a shop called People’s Place, when he was just 18 with $150 as an initial investment. The store, which sold “hippie bellbottoms and cool rock’n’roll type clothing,” was initially a smash hit but seven years on, in 1977, filed for bankruptcy.
In 1985, the budding designer moved to New York and with the help of backer Mohan Murjani, who owned Gloria Vanderbilt jeans, launched his own eponymous label — this time “very serious about logistics and business, to make sure we had a solid base”. In that, he succeeded. Three years on and the label had sales of $25 million, reaching $500 million by the mid-Nineties. In 1992, his became the first fashion business to float on the New York Stock Exchange and by the end of that decade, Tommy Hilfiger had expanded from a menswear label to a global lifestyle brand, with annual sales of $1 billion. “We’ve been a casual brand for over 35 years, so the casualisation of the world has suited us well,” he says modestly. “Our success, I think, was a mixture of luck, hard work and following through with our plan.”
Hilfiger sold the Tommy Hilfiger Corporation for $1.6 billion in 2006, by that time an umbrella for 14 product lines including men’s, women’s, children’s, accessories, fragrances, footwear, eyewear and home furnishings. Four years later, the Calvin Klein owner Phillips-Van Heusen snapped it up for $3 billion. Hilfiger remains the company’s lead designer, directing a brand that today has 13.6 million Instagram followers and operates more than 1,600 retail stores throughout five continents, including a Regent Street flagship in London.
In truth, his is a success story that’s got very little to do with luck. Not only does his preppy casual-meets-sportswear aesthetic have a broad appeal but Hilfiger also cleverly positioned his brand in the affordable luxury sweet spot, which allows it to sell aspiration in bulk. His expansion plans have been both aggressive and well-timed, and he’s positioned the brand firmly at the forefront of fashion’s dialogue on sustainability. Most pivotally however, Hilfiger pioneered the idea of celebrity collaboration at a time when glossy magazines still only put models on their covers, and successfully enmeshed his label with the music industry, giving it instant cultural capital.
“I was obsessed with music and musicians and still am and I wanted my brand to be connected to the music world. So, that’s what we did,” says Hilfiger, whose rock musician brother Andy introduced him to rap and hip-hop in the Eighties, before they were mainstream.
It was a music scene that had, to Hilfiger’s surprise, already adopted his designs. “Take your mind back to 1987, we’re a preppy brand. Classic, all-American, surfer-type dudes, and all of a sudden you see all of these hip-hop type kids, with boom boxes on the streets, wearing big baggy jeans slumped down to here,” he says, jumping up excitedly to demo, “with a big underwear waistband up here, with giant jackets with Tommy Hilfiger in red, white and blue, and logos, and backward baseball hats, gold chains, big sneakers unlaced, breakdancing on the streets.”
Artists including Mary J Blige, Snoop Dogg, and Run DMC were also rapping about his clothes. “They would freestyle during concerts,” says Hilfiger, smiling as he does his best rap: “‘I’m wearing Tommy, I’m wearing it right,’ I mean it was like crazy, this explosion.”
Hilfiger responded by designing even bolder, baggier and more oversized pieces, and by the time Snoop Dogg wore a Tommy-branded shirt on SNL in 1994, the hip-hop affiliation was cemented. “In some of the major cities like Chicago and Detroit, Miami, New York and LA, they’d get mugged for the clothes,” he recalls. “But now that crowd have gone to Gucci, Prada, Vuitton, because they want the most expensive.”
The rap association was so strong in the Nineties that it put some Tommy clients off. “A lot of my preppy customers went to this company called Abercrombie and back to Polo during this time,” says Hilfiger, who offset the loss of business by expanding into Europe. In 1996, he held his first European runway show in London’s Natural History Museum. Hip-hop trio Naughty by Nature rapped the soundtrack, while P Diddy, Coolio, Naomi, Kate and Karen Elson all walked the runway in baggy jeans, oversized T-shirts and bandeau tops in red, white and blue. “[Fashion critic] Suzy Menkes was sat front row saying, ‘I’ve never seen anything like this before’,” he smiles. “It was crazy.”
In more recent years, he’s evolved to collaborate with a broader genre of celebrity, launching sell-out collections with pop culture icons like Gigi Hadid (which ran from 2016 to 2018), Lewis Hamilton (from 2018 to 2020) and Zendaya in 2019. This year he’s working with Indya Moore, Romeo Hunte and Timberland. “I enjoy the creative and image-making and controlling the perception of the brand, which to me is its engine,” he says. “And an aspect of that is the people we work with, whether they’re the models or celebrities or people who make the brand look good.”
To debut the Tommy x Gigi capsule in 2016, he also reinvented the show concept with the launch of his big-budget see-now buy-now runway spectacle Tommy Now, which came this side of the Atlantic for the first time back in 2017 and returned again in February 2020 with a mega Insta-moment show at Tate Modern. Could there be another London event on the horizon, I wonder? “Yeah, why not!” he smiles. “Right now though we’re working on something very different, not something we’ve ever done in the past. Because I really think fashion shows need to change. They need to become fashion-tainment.”
These days, he’s less preoccupied with IRL events. Instead, his mind is focused on the metaverse. “We believe the real world and virtual world are coming together,” says Hilfiger, who has already designed virtual clothes — or skins — for video games like Animal Crossing and Minecraft, and is expanding the brand’s digital clothing wardrobe.
Perhaps the next Lewis Hamilton collab will arrive via Fortnite? “I’m always looking for what’s next, what’s new.”