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After 32 years in business, Tommy Hilfiger knows the long game and has played it well.

That he’s still actively in the game at all — at a point when many of his peers from the early Eighties are not — is no small feat. And not only that, he’s currently on a winning streak to boot. Of course, Hilfiger is incredibly wealthy, has been for a long time. But his numbers are not just healthy, they’re up — four percent in the second quarter. He’s one of the few designers to jump on the beast of a bandwagon that is see-now-buy-now and not be bucked off. Even more improbable and impressive is that after all these years Hilfiger has managed to achieve the highly elusive thing that fashion craves most, even if no one will admit it: At the moment, Tommy Hilfiger is cool again. Hard evidence is coming in February when the Vetements x Tommy Hilfiger collaboration drops.

Perhaps the coolest thing about Hilfiger is that there is nothing cool about him. Sitting in his gleaming showroom in the Starrett-Lehigh building in late August, he’s sporting a navy tailored suit and a fresh tan from his vacation aboard his yacht Flag with his wife Dee Ocleppo and Kris Jenner. He is nothing but happy.

“I’m excited that someone has noticed,” he says of the uptick in his brand’s pop-cultural currency. Among its premium competitors, Tommy Hilfiger is currently the most popular brand among Google searches. The aw-shucks smile and earnestness that originated in Elmira, N.Y., haven’t been filed down to fangs after three decades on this job. He still has the guileless air of someone who can’t quite believe his good fortune. There’s no irony. There’s no edge. And yet the funny thing is, Hilfiger is a bit of a gamblin’ man.

Taking a risk on a ballsy, legendary ad campaign by George Lois in 1985 is now part of Hilfiger’s brand lore. More recently, one of his biggest bets to pay off is Gigi Hadid. He wasn’t as early to embrace her as Jeremy Scott, Tom Ford or Karl Lagerfeld, but Hilfiger still got to her early in her rise. He fell in love with Hadid after casting her in his fall 2015 show, and he fell hard, taking a bigger position on her than just catwalks and campaigns. In late 2015, he signed her as a global brand ambassador and codesigner on a capsule collection based on her style with his and her names on it.

“We engaged with Gigi at the beginning of her trajectory, and I think it was just a feeling that we had that this girl was going to be beyond what any other model or any other ‘It’ girl could be,” said Hilfiger.

It has been a whopping success, taking him away from the preppy-with-a-twist style for which he’s known and more toward hot-twentysomething-with-a-sense-of-style territory. When the Tommy x Gigi collection debuted as Hilfiger’s first see-now-buy-now show in September 2016, it generated 900 percent increased traffic to in the 48 hours following the show. There were 2.2 billion social media impressions surrounding the event, and the halo effect was double-digit sales growth in all women’s categories in every region.

“If you go with your gut in this business, sometimes it works, sometimes it doesn’t work,” said Hilfiger. “This time it worked beyond our expectations. Way beyond.”

“That’s so sweet of him to say,” said Hadid upon hearing how much credit Hilfiger gives her. “I’m glad he feels that way because it was a big risk to take. It’s done really well and the world has embraced the collection. I wanted to make something that connected with people of all different levels. It’s been really nice to see the teens coming to the meet and greets, but there are also stylists in the industry who are older and are like, ‘Oh, I bought this and this.’ It’s surprising but really cool. I think that’s what Tommy wanted.”

This was a big move for Hilfiger. He’s worked with many more-than-a-model models including Britney Spears, Kate Hudson, Kidada Jones, the Richards daughters, Lizzy Jagger and Ivanka Trump. Other current ambassadors include The Chainsmokers, but no one but Hadid had ever been elevated to top billing of a codesigner role. Why her?

“I think a lot of it had to do with her personality,” said Hilfiger. “She’s very sporty, healthy, kind, nice, fun, funny, friendly and she has a spirit that is very much in keeping up with what our brand values are. It seems like it was a marriage made in heaven.”

To some extent, Hilfiger’s alignment with Hadid comes down to him being more of a cultural seer than he’s ever been given credit for.

“Tommy just has a nose for that,” said Avery Baker, the firm’s chief brand officer, who’s responsible for steering the mammoth marketing machine of the PVH-owned company. “He just said, ‘I think she’s going to go all the way.’ I think it’s that amazing combination of who she is and the time that we’re in and the fact that the power of what we’re seeing in social is really taking off. He said, ‘Let’s go for it,’ and so we did.”

They didn’t just go for Gigi. They doubled down on several levels, resetting the business to a see-now-buy-now timeline and cooking up a fashion show extravaganza for the runway show, taking over a pier in New York City and changing it into a working carnival called Tommy Pier that was open to the public for a night. Essentially it was a product launch on steroids.

“I would say, for over five years we’ve been talking about opening our fashion shows to the public. Every time we have a show we get calls from students, from people who are not in the fashion business asking if they can either buy a ticket, or come to the show,” said Hilfiger. “In listening to the Millennials, we kept hearing they wanted immediate gratification. In addition to the immediate gratification they wanted exciting experiences or an exciting experience. So we brainstormed and we thought, look, if we had a buy-now-wear-now fashion show with Gigi headlining, with her collection, and it could be immediately available, and we would provide an incredible, memorable experience that would be disruptive in the industry, unconventional and breakthrough, we should do it.”

It took the company a year to realign its back end and supply chain to accommodate an immediately available collection. What had to have been a multimillion-dollar investment many times over for the whole #Tommynow production was worth it. The second iteration of the Tommy x Gigi shebang was called Tommyland, and took place in Venice Beach in February. The third is scheduled for today in London. The theme of today’s show is “rock ‘n’ roll circus.” At the time of the first Tommy x Gigi show, she had around 13 million Instagram followers. Now she has 35.7 million.

Even before he doubled down on Gigi and instant fashion, Hilfiger seemed to see where the all-powerful social media winds were blowing. He’s always loved a theme and a tricked-out set to match, but about three years ago he decided that fashion shows were boring. He upped the ante by staging a rock fashion show for spring 2014 and saw the digital imprint explode. The kids wanted Instagrammable moments, so Hilfiger delivered. The next season’s set was a nearly to-scale re-creation of Basil’s Bar in Mustique, where Hilfiger has been a regular for 30 years. The key photo was a horde of bikini-clad Insta-models, including Hadid, marching out into a lagoon. It was charmingly over the top and the clothes were cute.

At the same time Hilfiger has focused on catering to the digital Millennial audience, another trend has swept through fashion with secondhand effects that worked in Hilfiger’s favor. High fashion’s obsession with Nineties streetwear gave the designer a goose of relevance unrelated to shiny, happy nouveau models and see-now-buy-now. Suddenly his vintage logo-heavy flag gear that was a uniform of the Nineties hip-hop scene was trading on resale sites like Grailed. The site’s brand director Lawrence Schlossman said that Tommy is one of the most popular brands sold under Grailed’s Core section, alongside Polo and Nautica.

“We’re talking vintage stuff, not necessarily new Tommy that I could walk into Macy’s and buy tomorrow,” said Schlossman. “And we’re talking about thousands upon thousands of items.”

Though there’s something viral and organic about the vintage streetwear sector, the Tommy team saw the trend coming — they have big data at their disposal. “We had a lot of debates internally on how to handle it and how far to go on embracing the Nineties streetwear trend,” said Baker.

A cautious approach was understandable. Hilfiger’s original Nineties street moment was a tricky one. He went too hard on the hip-hop look and it came back to bite him. Who remembers Spike Lee’s “Bamboozled?” Hilfiger won’t make that mistake again.

Rather than go wide reissuing Nineties heritage stuff, the brand kept distribution tight with a heritage capsule under Tommy Jeans priced above the company’s most mass product. “That approach really paid off,” said Baker. “Keeping it special is what has made other very influential brands such as Vetements interested in partnering with us.”

To that end, after being introduced to Guram Gvasalia, chief executive officer and brother of Vetements designer Demna Gvasalia, a Vetements x Tommy Hilfiger capsule is on its way. He’s been kissed by one of fashion’s key imprimaturs of cool. “I associate [Tommy] to my adolescence,” said Demna Gvasalia. “In the Nineties it was really cool in Russia to wear Hilfiger, there were even so many fakes.”

The momentum is undeniable. Macy’s is still the exclusive U.S. distributor of Hilfiger’s sportswear line, but the brand’s other premium collections are picking up new accounts including Bloomingdale’s, Saks Fifth Avenue, Harrods, Selfridges and Urban Outfitters. On the men’s front, Hilfiger did something different, taking a spot at Pitti Uomo in Florence this summer.

“You have to be really, really well aware of the timing aspect,” he said of his approach to big trends. “You have to know when to hold back. I think you have to know when to produce, and it’s not a science and something that’s learned. It’s instinct and we’re going with our instinct now. But we have a lot more data than we’ve ever had, with big data we love. We’re a lot more intelligent than we were in the past because of artificial intelligence, and we’re depending on artificial intelligence to tell us where he or she is going and what they want next.”

The streetwear trend will eventually wear itself out, and though Hadid renewed her Tommy x Gigi contract for another two seasons, that won’t last forever either. That’s OK, said Hilfiger. His $6.6 billion brand will go on without them. There will be new trends and new faces. One of them comes up during a conversation about summer vacations — she’s a 14-year-old DJ who has played in Ibiza and St. Barths.

“We dressed her and her friends in Gigi,” said Hilfiger. Isn’t 14 a little young? “We have to begin to look at her age group because they’re Generation Z. They’re next. We cannot ignore that group,” he said.

Hilfiger credits his own children with keeping him connected. “My son is into rap and hip-hip. My daughter Ally is into vintage fashion and my daughter Foo Foo [Elizabeth] is into Vetements and has her own brand Foo and Foo,” he said. Constantly figuring out what the kids want must be exhausting, but it’s the name of the game for Hilfiger.

“I was always afraid of losing the youth,” he said. “Keeping a brand youthful is a lot more work and takes a lot more creativity. But it’s very exciting.”

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