Tommy Hilfiger: National Treasure

Nearly 40 years into his fashion career, Tommy Hilfiger is showing no signs of slowing down. In fact, he’s revving his way into the metaverse.

Tommy Hilfiger signs onto Zoom and quickly confesses that he’s not into the following:



TikTok fads.

Leaving the party early.

This admission sheds some light on the mindset of one of America’s most successful designers, and why the 72-year-old Aries is “still in love” with running his globally recognized fashion label, which includes clothes, shoes, underwear, eyewear, a partnership with ThredUp to encourage #vintagetommy finds, and, most recently, a designer foray into gaming.


TOMMY HILFIGER photographed by Greg Kessler

Hilfiger says this with a sunny disposition that matches his backdrop: A light-filled Floridian manse with stone-carved arches and a clear view of an even clearer sky. When Hilfiger leans into the camera (which he does often, especially when excited), there’s a halo effect that looks like he’s being filtered or Facetuned. But that aesthetic wouldn’t jibe with Hilfiger’s number one rule: “Being fake, with people or designs, just doesn’t work. Being authentic to your vision is what helps you win.”

And Hilfiger is familiar with winning. He started his fashion journey as a teen from upstate New York who would drive a Volkswagen Beetle into the city, cram it with Garment District denim and vintage leather coats, and return to his hometown to resell the wares. Eventually, he and his friends opened a store, People’s Place, which became a cultural hub and hangout. “It was one of the best experiences of my entire life,” Hilfiger says of that era. “It was so much fun and it was so cool. I dream about that store a lot. Still.”

from left: Dylan and Eliza wear TOMMY HILFIGER


From there, it was on to India, where Hilfiger learned the denim design and manufacturing business from the ground up. In 1985, he was famously fired from a denim director position at Jordache and began sewing his own label instead.

“I think I’ve always succeeded, creatively, because I can’t turn off my mind,” Hilfiger says. “It’s always a thrill to create something… And I like the competition in fashion! It’s very competitive, and that competition gives endless opportunities.”

One of those opportunities came when Hilfiger met ad man George Lois. “He created the whole MTV launch campaign [in the Eighties] and I thought that was so genius,” Hilfiger recalls. “So I was like, ‘What should we do?’” Lois came back to Hilfiger with a billboard proposal: A game of hangman that proclaimed “The 4 great American designers are… ” with prompts to fill in “Ralph Lauren,” “Calvin Klein,” “Perry Ellis,” and Hilfiger himself. The billboard would show no clothes, just the label’s now-famous flag logo.

from left: Haley, Dylan, Eliza, Ingrid and Kit wear TOMMY HILFIGER

“When George first proposed that ad, I thought, ‘I’m going to look like such a loser!’” Hilfiger exclaims. “I said, ‘Look, I just want to do a great-looking model at the beach. A cool, untucked shirt, hair blowing in the wind.’ And George goes, ‘That’s a stupid idea! It would take you years to make your mark with a traditional campaign. You have to do something disruptive.’ That was the first time I’d heard anybody say the word ‘disruptive’ in terms of fashion. Suddenly I got it. Things clicked. And basically it lit the brand on fire.”

In 1988, three years after Hilfiger launched his eponymous label, sales reached $25 million and the brand became synonymous with the American classics: varsity jackets, logo tees, and lots of denim. Fans loved Hilfiger’s friendly, familiar logo, and the one time he veered from it, sales fell hard. “I did a collection of very modern, minimalistic clothes. No trim, no detail—simple. It was a disaster!” He shakes his head. “Lesson learned—the minute I went back to trusting my design sense, the business got back on track.” (According to PVH, the parent company that also owns Calvin Klein, Tommy Hilfiger’s global sales reached approximately $9.1 billion in 2022. “Back on track” indeed.)

Embracing and scouting next-generation talent over the years has also proven invaluable to building Hilfiger’s beloved world. In the late Eighties, the designer signed DJ Spinderella as an ambassador before her group, Salt-N-Pepa made it big; he enlisted the stunning R&B artist Aaliyah as one of his first womenswear models and sponsored an emerging Lenny Kravitz on a major tour. Mark Ronson was a DJ for the brand long before his Oscar for A Star Is Born. Kate Hudson and Josh Hartnett were early campaign models, as was Britney Spears. “She asked us for some jeans and we said, ‘Well, why don’t we sponsor your tour?” Hilfiger says. “We shot her the day that her song Baby One More Time went number one… and she just took off… She’s had her trials and tribulations but she’s a mega-talented star. I hope she has a comeback.”



Pre-pandemic, Hilfiger created well-received collections with Gigi Hadid and Zendaya. “I look at fame in sort of a different way than I used to,” Hilfiger says. “Because now with social media you can be known, but what for? For me, it’s more like F.A.M.E., which is ‘fashion, art, music, entertainment.’ And of course, sports. That’s what I use as the engine behind my brand and what’s powering us, because that is culture.”

Hilfiger’s boldface collaborators include SZA and H.E.R., plus friends like Kendall Jenner. “I’ve been pretty close to the family for many years, so I’ve known Kendall since she had braces,” he says. “I remember her sitting at the dinner table saying, ‘Mommy, I really want to be a Victoria’s Secret model.’ And that was a real wish because Kris then took her to Australia to meet the people who were shooting the Victoria’s Secret campaign! Oh my goodness, she must have been, like, 14… But she is a Tommy girl because she’s very bright, very sweet, extremely talented, and believe it or not, she’s also very humble.

from left: Ingrid and Kit wear TOMMY HILFIGER


But you don’t have to be a Kardashian, or even keep up with one, to play dress-up for Hilfiger’s latest endeavor, the app-based game FashionVerse, which launched in January. Using AI technology, it’s a styling game created with the tech platform Tilting Point. To win, users complete a series of “get ready with me” exercises using various fashion brand’s designs as game-play options; other users vote on whole virtual outfit or mood board is the best. Besides inspiring the concept, Hilfiger was instrumental in overseeing its execution. “You can choose many different outfits and many different ways to style an avatar,” Hilfiger says. “But the avatars themselves are very diverse, a non-negotiable.  We assign them to you, and every day you’ll get a different character to style. They could be older or younger, maybe they could have a disability. They’ve all got different hairstyles, hair colors, and skin colors. It’s a blast.”

Being inclusive was a mandate for Hilfiger, one of the only major designers to make adaptive clothing for the disabled community. “It’s always been important to me, as a fashion brand, to care about people’s lives,” Hilfiger says. “We embrace diversity because that’s what we’ve done for 40 years.”

It would be hard to match Hilfiger’s unrelenting enthusiasm as he continues to forge ahead IRL and in the FashionVerse. “I hope to work in fashion forever,” he says. “I love the challenge. I love the creativity. I love it all.”


Instagram: @tommyhilfiger


Fashion Editor ROGELIO F. BURGOS



at Viva London, HALEY HALTER at Elite London, and ELIZA RUTSON PANG at Premier Models

Hair HIROKI KOJIMA at Caren using Amika

Makeup MEG KASHIMURA using Clé de Peau Beauté

Photographer’s assistants JOSEPH CONWAY and ETHAN HUMPHRIES

Fashion assistants ELI RICHARDS and EMILY GLEESON

Hair assistant AKIRA

Makeup assistant NATSU TOMONAGA


Executive producer CHLOE MINA

On-set producer ABI FLEMING



Clothing and accessories throughout by TOMMY HILFIGER


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