KING of COOL

Tommy Hilfiger's new collection offers a fresh take on his signature maritime style

- GEORGIE MCCOURT

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.

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.