Fashion is a fickle beast, and no one knows that better than Tommy Hilfiger. For this reason, perched on a navy sofa on the ninth floor of his flashy 285 Madison Avenue, New York office, the man who built a billion dollar company in part by bringing streetwear to the masses is happily ringing its death knell.
“We’ve evolved out of streetwear,” says the 72-year-old designer, of the baggy jeans and splashed logo tees he borrowed from the skating, surfing, hip-hop devotees and has been a staple of his brand since the Nineties.
Ironically, today he is kitted out in a full, white, branded tracksuit and boxfresh white trainers, “but I am catching a flight to Palm Beach later, this is just comfy,” he quips. “Streetwear had its moment. We did it in the early Nineties and then again just recently. Now it will take a break and come back in a different way in 10 years.”
This was the take away from his Friday night New York Fashion Week show behemoth. There was good reason to go big — the King of the Big Apple was back, following his two-year show hiatus. “New York is where it all began, in 1985, almost 40 years ago. This is home. And when we show at home, we want to do something special,” he says, all-American veneers gleaming.
And special it certainly was. At about 8.30pm, in Grand Central Station’s Oyster Bar, a 400-strong crowd had made it through NYPD-controlled crowds who hoarded at the entrance and models started to stomp about the wooden booth tables, flush with dirty martinis and lipstick stained champagne flutes.
The usually gingham tablecloth-strewn restaurant had been royally Hilfigered — a fresh navy carpet was rolled out, and framed red, white and blue logo flags hung on walls. Plenty of Londoners made the trek; sat front row was Peckham actor Damson Idris, Shepherd’s Bush-born rapper Central Cee, Bollywood star and Notting Hill resident Sonam Kapoor, comedian Gstaad Guy and Romeo Beckham’s model beau Mia Regan.
It was the first headline show of New York Fashion Week, and the anticipation in the room matched that of the city’s sports bars on Super Bowl Sunday, which would come two days later. As for the clothes, Hilfiger went back to zero with the style he cut his teeth with — all preppy everything. “We wanted it to be classic American cool and preppy, but lifted up and polished,” he says. The opening look, floppy, wide beige tailored slacks worn with an exaggerated collar button down and stealth wealth grey, worsted wool cap, set the tone.
What followed looked like the sixth form heartthrob — girls in Prince of Wales check mini skirts, navy pea coats and polished loafers; boys in their skewed, striped ties, rugby shirts and backpacks slung on one shoulder — times 59. Or, in New York terms, like they had stepped out of Gossip Girl, the TV series which followed Upper East Side elites through prep school, and which aired in 2007 with an opening scene set in Grand Central.
True to life, real rich kid and nepo baby Scarlet Stallone, the 21-year-old daughter of action star Sylvester, walked the catwalk. “He’s a good friend,” says Hilfiger of her father, who was cheerleading from the front row. “It’s school girl, Ivy League, collegiate,” Hilfiger says. Why? Because we are witnessing the return of posh, he thinks. “People want to look like they’re wearing expensive clothes. It’s becoming more grown up, more sophisticated. The pendulum swings this way and that way all the time.”
You only need to look at the unbridled success of Saltburn, Emerald Fennell’s romp of a film obsessed with the lives of the crumbling British aristos, to understand there’s appetite today. On the runway, notes of the British upper classes came through — most notably in the riding boots borrowed from huntsmen, complete with the wide-ankle fit you would sooner see in stirrups and surrounded by hounds in the Cotswolds, than on a trendy New York exec.
“Many of [those wanting to look posh] can’t afford to shop in the luxury market. If you look at the prices of Vuitton, Prada and Loro Piana, it’s unreachable,” he says. His mid-range offering, which to touch feels sturdy and well fabricated (“the quality is fabulous,” he chirps), have been made to fill that gap.
It is testament to his persevering business acumen which has defined Hilfiger’s bolshy rise; a story that started with an 18-year-old student flogging jeans in Elmira, a city in New York state, and graduated to an eponymous label, launched with the backing of Indian textile magnate Mohan Murjani, when he was 34.
Three years later, in 1988, he hit sales of $25million. By the mid-Nineties, as the brand boomed in the hip-hop and rap community, that number quickly multiplied to $500million, and before the turn of the millennium he had hit the $1billion mark. In 2006, Hilfiger sold the company for $1.6billion. He remains the company’s lead designer today, and appears motivated as ever to claw in new customers.
Celebrity collaborations have been his most recent golden ticket, and have counted lines designed with Gigi Hadid (from 2016), Lewis Hamilton (from 2018) and Zendaya (from 2019). In 2024, Sofia Richie, the model daughter of singer Lionel, has taken the reins. “We are always looking at who might be next,” he says. “And Sofia is going to be the next big It girl in the world.” Her flashbulb-blinding entrance to the show, British music executive husband Elliot Grainge in tow, was typical Hilfiger fashion-tainment, as he calls it.
“A normal fashion show is antiquated,” he says, and adding excess flair to the catwalk is an industry standard he pioneered. This is true as far back as 1996, when he expanded to Europe with a blow-out show at London’s Natural History Museum. Editors were sent into a frenzy as rapping trio Naughty By Nature performed, and Kate Moss, Naomi Campbell, Karen Elson and P Diddy weaved around him.
The format was so good it stuck. On cue, Friday night’s spectacle ended with a surprise performance from Grammy-winning singer Jon Batiste, who performed his hit Freedom. “You always need to twist like that,” he says. “If it’s just a plain fashion show, everything feels very boring.”