Enduring Americana: Tommy Hilfiger on the secret to his company's 40 years as a leading lifestyle brand

Tommy Hilfiger has always been a master of a certain kind of American mythmaking. He was probably the first person to introduce the world to the aspirational Americana of glossy campuses, convertible Mustangs and endless East Coast summers.

Since launching his eponymous brand in 1985, Hilfiger has turned varsity stripes, nautical preppy codes and a deft sense of the pop culture zeitgeist into a multi-billion-dollar lifestyle empire. Unlike many of his peers, he’s never looked at fashion as a fortress of exclusivity – he has always made it feel like a block party.

“I think a laid-back element is what people want to show up in,” Hilfiger tells me during our chat in the newly refitted store at Mall of the Emirates. He’s seated with the ease of someone who long ago stopped needing to prove himself.

Even at 74, Hilfiger is still at it, as comfortable walking a store floor in Dubai as he is hosting front-row celebrities in New York. “The reason I’m where I am today is because I surrounded myself with incredible people.” He says it like a mantra, going some way to explaining his longevity.

Long before the term “brand collaboration” had PR departments salivating, Hilfiger was making overtures to musicians. In the 1990s, when streetwear was still largely subcultural, he made the bold move of dressing hip-hop stars such as Snoop Dogg and Aaliyah in his oversized logos. It was a move that scandalised the country club set and electrified everyone else. The result? A brand that wasn’t just seen, but worn, lived in, sung about. The clothes didn’t just sell, they belonged to the culture.

Hilfiger has built a career not only on good taste, but good timing. He knows when to amplify tradition and when to deconstruct it. “I don’t believe in fashion rules,” he says and perhaps that’s the secret to staying relevant across decades – knowing which codes to keep, and which to tweak.

“There’s a lot of exciting things going on in the culture,” Hilfiger says about what keeps him motivated. “Fame, fashion, music, sport. There’s never a dull moment. And that’s all part of the DNA. And I’m still having fun.” He says the last bit with a knowing smile.

He drops names like a man who’s earned the right to: Zendaya, Lewis Hamilton, Shawn Mendes. But these aren’t just a list of friends from dinner parties. These names that have recently collaborated with his brand are proof he still understands the zeitgeist 40 years on. “There’s always someone on the wishlist,” Hilfiger says of any potential future collaborations, “but I can’t reveal that".

He’s as much a tight-lipped business man as he is a creative. And there’s no qualms about that. “I started my business when I was still in school. I opened a shop for people who loved music and fashion,” he says of People’s Place, the shop he opened in Elmira, a small town in New York State. With $150, he drove into New York City to buy 20 pairs of bell-bottom jeans to sell in the store. It was a place where he could sell “the cool styles we couldn’t find in our small town”.

“In those days, It was the late 60s. It was a time when rock was exploding. During the summer of Woodstock, the English groups were touring all over North America. People had never seen long hair and bell bottoms.” But that electric feeling wasn’t enough. He didn’t want to sell other people’s clothes. He found a business partner and well, the rest is history.

The word “fame” comes up often in our conversation. Not as an aspiration, but as a kind of currency – something to be exchanged for relevance. He classifies it as a category that almost sits above music, cinema and sports. And when I ask what has changed most since he started, it is also linked to how that currency gets traded: “Social media,” he says plainly. Does it influence his process? “We’re on our own journey,” he replies, like someone who’s learnt that it is just one more thing to adapt to.

“I notice you’re wearing olive green,” he says pointing to my workman’s jacket. He tells me there’s something in the collection I’d like.

When we’re done with the sit-down, he takes me around the store looking for the piece. He’s moving through the racks like a salesman on the shop floor. Beyond the iconic collaborations and mega-deals, that’s the true key to his longevity.