Courtesy of Tommy Hilfiger
The man at the helm of one of the world’s most successful fashion empires is talking about how he failed at school. “I was a terrible student,” says Tommy Hilfiger, the 73-year-old pioneer of classic American cool.
“I didn’t realise I was dyslexic until later in life. I just thought I wasn’t very smart.”
Hilfiger, the second of nine children, was born into a working-class family in Elmira, upstate New York.
“My parents couldn’t afford to send me to college. I thought, ‘If I’m in business myself, I’m going to make it work,’” he says.
The Birth of the Tommy Hilfiger Brand
It’s the day before his spring/summer 2025 runway show – set aboard a decommissioned Staten Island ferry owned by Saturday Night Live’s Colin Jost and alum Pete Davidson – and Hilfiger is recalling a journey that began with $150 in savings and a dream.
In 1969, at 18 years old, Hilfiger bought 20 pairs of bell-bottom jeans on the streets of New York and drove them five hours upstate to sell them from the boot of his Volkswagen Beetle.
Soon after, he opened his first store, People’s Place. “I sold concert tickets, records, cool clothes, and had my brother’s band practising in the basement,” Hilfiger recalls. That early venture wasn’t just a store, it became a community hub where young people gathered to discuss music and fashion.
In 1985, he launched Tommy Hilfiger, the brand that would redefine American fashion.
From Prep To Street: Hilfiger’s Hip-Hop Revolution
His breakthrough came in the 1990s, when Hilfiger’s preppy Americana aesthetic unexpectedly resonated with hip-hop culture. “The brand went from being sort of a preppy all-American brand to a brand that attracted hip-hop rappers, surfers, skaters,” he says.
Embracing this cultural shift, Hilfiger leaned into bold logos and oversized silhouettes, turning his customers into “walking billboards”. His clothes were worn by everyone from Mick Jagger and David Bowie to Britney Spears and Usher, creating a celebrity fan base long before social media made such cross-cultural appeal commonplace.
Today, four decades after launching his brand, Hilfiger maintains the restless spirit of that teenage entrepreneur from small-town New York state.
He openly talks about how he has learnt to use attention deficit disorder as a creative force.
“I have ADD so I could be working on something but thinking about another thing,” he says. “But I always come back into focus because I know that if I concentrate on priorities, I’ll get there.”
And even after so long in the game, there’s not a hint of complacency to Hilfiger. “It’s never enough,” he says.
Despite his success, he speaks about the future as though it’s his first year in business. “I keep thinking that I’m going to become successful in the future, even though other people tell me that I’m successful,” he says. “I want better stores. I want better advertising. I want better fabrics. I want better quality. I just want everything to continue to get better and better and better.”
The Ever-Evolving American Dream
Tommy Hilfiger’s spring/summer 2025 collection marks a return to his nautical roots, seamlessly blending classic influences with contemporary trends. The lineup features higher waists, wider legs, cropped tops, and oversized jackets, offering a fresh take on the signature maritime style that has defined Hilfiger’s brand since 1985.
“We’re revisiting the nautical and maritime inspirations that have always been part of our identity,” Hilfiger explains. “But for 2025, it’s a remix – effortless summer style with a confident edge, ready to move from the ferry to the city streets.”
The collection strikes a balance between preppy, collegiate charm and modern sensibilities, showcasing Hilfiger’s keen ability to capture the cultural zeitgeist.
The grand finale of the show was a reminder of this, with Wu-Tang Clan’s Ghostface Killah, Method Man and Raekwon, along with Questlove, curating the electrifying soundtrack – a testament to Hilfiger’s status as a true cultural icon.
As this interview ends, Hilfiger reflects on the idea of the American Dream, a concept he’s often associated with. “I believe I’ve achieved the American Dream, but it’s never truly finished because there’s always more to strive for,” he says.
“The American Dream is about working hard, persevering, and staying committed to your path. It shows that you can succeed if you keep going. I always tell students that if you have a dream, go after it. Do what you love, not just something to pay the bills. It makes all the difference in the world.”
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