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Four decades ago, Tommy Hilfiger opened a small store in upstate New York with $150 and a rack of bell-bottom jeans. What followed wasn’t just the making of a fashion brand—it was the making of a modern American legacy. Now, as he celebrates his brand’s 40th anniversary, the designer sits down with GRAZIA at ‘The Hilfiger Resort’ in Canouan, reflecting on his journey with the kind of clarity that only comes from a life spent at the forefront of culture.
“I look back at the very beginning, and when I first started out… I did everything—designed the clothes, chose the buttons, the zippers, worked in the factories,” he recalls. “I sketched everything out myself. I had a vision and I had this dream, and I thought, ‘well, maybe I’ll be an American designer, making menswear in America,’ and then, it went from menswear, to denim, to sport, to womenswear, to children’s, to accessories. I thought, ‘I’m building a global lifestyle brand’. But I never lost sight of my North Star.”
That North Star—an essential colour palette of red, white and blue, and an unwavering preppy meets casual sensibility—has kept Hilfiger’s compass steady even as the industry around him endlessly reconfigured. Where others followed trends, Hilfiger doubled down on timelessness, refracting the codes of Ivy League classics through the lens of street culture and accessibility. As hip-hop icons wore varsity jackets with oversized logos, as style bloggers captured their chinos and crewnecks in downtown cafés, Hilfiger’s vision began to stand for something beyond clothes. Something that could transcend the usual boundaries of people and places.
But make no mistake, the brand has journeyed through many chapters, thanks to its founder’s passion for keeping his finger on the pulse. With an affinity for reinvention, it has always been more instinct than strategy. “It’s kept us on track,” he says. “But it always has to be fresh, reflective of the times.”
Back in the 1980s, amid a New York scene exploding with punk, disco, and New Wave, Hilfiger’s tastes leaned elsewhere. “I didn’t love ‘80s fashion,” he admits. “I loved designing for the ‘70s, and I made it a point not to become entrapped in the trends of the decades.” While others succumbed to shoulder pads and lycra, Hilfiger focused on staying different—something that, in hindsight, gave his work an enduring edge. “I wanted to be an alternative, in a sense, not to fall into the mainstream of what everyone else was doing in fashion.”
It’s a philosophy that’s followed him throughout the decades. Whether it was the oversized rugby shirts of the 1990s, the crisp minimalism of the early 2000s, or the celebrity-fronted capsule collections of the last decade, each moment in the brand’s journey has carried that subtle contradiction: comfort and polish, aspirational yet accessible, retro yet always relevant.
“My focus was on comfort and fun and wearability,” Hilfiger explains, noting his desire to bring style to the masses. “Affordable is a big word because so many products and so many designers are so overpriced,” he adds. “I wanted people to be able to buy something of quality that they can have in their closets forever, but something that was also special.”
From Cape Cod to catwalks, the Tommy Hilfiger brand has long been a masterclass in aspiration made tangible, without ever compromising on craft. “I really mapped it out that way,” he says. “I really wanted it to be for everyone.”
That inclusivity didn’t just play out on the shop floor, but across the brand’s boldest moves. In 2016, long before digital influencers were seated front row, Hilfiger’s collaboration with Gigi Hadid redefined what a fashion show could be—interactive, inclusive, internet-breaking. Three years later, he partnered with Zendaya for a Harlem showcase that has since gone down in history as a masterstroke of modern fashion storytelling. These weren’t just collaborations—they were cultural forecasts.
And then came the business shakeup. In 2017, while most brands adhered to the traditional fashion calendar, Hilfiger adopted a see-now-buy-now model, making entire collections available for immediate purchase. It was a decision that few had the nerve to make, but for a designer so attuned to the tides of consumer culture, it was a no-brainer.
And indeed, the collections of late reflect this evolution. “Dressing up is back,” he said ahead of his Fall/Winter 2024 collection presentation in the Big Apple. “People are moving away from streetwear into a more polished look. It’s in the air—I can feel it.” And while the pillars of the brand—preppy knits, button-down shirts, well-cut chinos—remain firmly in place, they’ve been elevated to reflect a temperature check. The palette is quieter, the silhouettes sharper. Gone are the big logos and graphic prints; in their place, cashmere blends, relaxed tailoring, a kind of stealth wealth at a digestible price point.
“We grew up in this casualisation of the world, and our clothes remain casual. But we’re becoming more elevated and more refined,” Hilfiger explained when GRAZIA previously caught up with him in New York.
It’s this constant balancing act between familiarity and freshness that has kept the Tommy Hilfiger brand relevant, even as many of its peers have faded. At a time when consumers are craving quality over flash and logos, Hilfiger’s refined Americana feels like an antidote. And with his global lifestyle empire expanding—menswear, womenswear, children’s lines, accessories, even a host of philanthropic ventures—his vision has resonated far beyond the runway. Still, the empire has a long way to go, according to the man who built it.
“I’m really proud to have built a globally recognised brand that continues to grow and evolve, and still has so much opportunity left,” he says. “There’s an unlimited amount of opportunity for us.”
Undoubtedly, it is this insatiable desire to keep growing that has enabled him to succeed so prolifically. After all, he learned a lot the hard way, too. “I went bankrupt when I was very young and starting out,” he says. “But it taught me how to focus on the business of fashion.”
“I really believe that in order to be successful, you have to understand the business,” he continues. “There are many talented designers who should be at the top of the heap, but because they don’t understand business, they fail. I think that that’s a mistake that fashion schools make by not teaching the creatives anything about business.”
To talk to Tommy Hilfiger is to hear the steady drive of someone who’s never really stopped moving forward. Always taking the old red, white and blue—and season after season, finding infinite ways to make it new again—the designer still views success as something to aspire to.
“We’re almost there,” he laughs. And as we sit in a room nestled in paradise, surrounded by his creations that are the culmination of four decades of design, the sentiment is an inspiring one, one that urges us to always keep growing.
“I’d like to do a lot more… I’m not finished.”
