When approaching the Tommy Hilfiger headquarters on Madison Ave, one is quickly reminded of what an institution the designer’s brand has become, not only in the fashion industry but in culture-at-large. A flag bearing the brand’s instantly-recognizable emblem waves above the main entrance of the 26-floor tower, an effective metaphor for the fashion empire Hilfiger has built up over the last four decades. 

From being an ambitious newcomer to the NYC menswear scene in the early ‘80s, to becoming one of the world’s most ubiquitous labels in less than 50 years, Hilfiger’s legacy is a testament to his sharp creative instincts and his ever-firm finger on the pulse. Meeting such a legendary designer in the walls of his own domain may compel one to use a formal address like “Mr. Hilfiger,” but if you do, he will gently correct you: “Call me Tommy.”

After presenting at famous NYC landmarks including the Staten Island Ferry (SS25) and Grand Central Terminal (FW24), Hilfiger continued the tradition for SS27, this time bringing the runway closer to home than ever before at The Plaza Hotel. The day before he made the grand return to his residence of more than a decade, the designer mused, “That’s iconic New York.” He reminisced fondly about living in the Plaza Hotel’s domed penthouse: “So many pass through the doors, so you see a lot of different people. People coming from Hollywood, sports stars, music stars, families, all different kinds,” he said. “There’s something about it that has that charisma, that effect.”

That dynamic mix of people he described was certainly reflected in the show’s guest list. The star-studded crowd, including supermodel Kate Moss and Knicks players Karl-Anthony Towns and Josh Hart sitting front row, extended to the runway, which was led by Gigi Hadid and closed by Romeo Beckham. At the finale, a surprise performance from emerging electro-pop star Slayyyter brought a sharp edge to the show, serving as the unexpected cherry on top of a roster of heavyweight talents. But far more than surface-level celebrity association, the far-reaching support Hilfiger receives across fashion, art, music, entertainment, and sports comes from a deep embrace and respect for cultural tastemakers, which has been integral to the brand from the start.

To understand Tommy Hilfiger today, you have to understand how he began. He started designing his debut collection in 1984, taking the classic prep he knew and recontextualizing it. “I thought, why don’t I take this prep and remix it? Why don’t I make it oversized, make it relaxed, add new details, and make it really cool? And that’s how I started in 1985,” he explained. While he still calls prep “the backbone of the brand,” it’s never been about distilling a static idea of the aesthetic, but instead reimagining its conventions and imbuing its notions with new meaning. 

By the ‘90s, he shared, “All of the rappers, hip-hop kids, athletes, preppies, surfers, skaters, and even the guys climbing in the Rocky Mountains with gear were wearing it. And young women started wearing the men’s, too.” The designer went on to recall the beginning of his working relationship with hip-hop stars: “What happened was my brother Andy said, ‘You have to hear this music,’ and they were rapping about Tommy Hilfiger.” The discovery triggered showroom invites for musicians like Grand Puba, the Brand Nubians, and Sugarhill Gang. “We would say, ‘What would you like?’ And they would put it on and wear it out and go play in a venue that night,” he shared.

Perhaps most famously, Snoop Dogg wore a Tommy rugby shirt on stage at SNL in 1994, and Aaliyah was seen pretty much everywhere wearing the brand. “I thought this was fantastic because I love music, I love musicians, I love the culture,” he said. “I loved the idea that we could actually dress these people and then see them on stage or have them sing about it in the music. That moment in time was a game changer.”

This collision between fashion and music became instrumental not only to Tommy Hilfiger’s future evolution, but to how the industry operates as a whole. Once novel, the influence of hip-hop and streetwear on designer fashion is now integral, with many luxury maisons welcoming rappers and streetwear designers into top creative positions. Hilfiger understands this, and it’s why he continues to honor this era of his career and keep his affinity for reinvention alive.

In a similar spirit to his early philosophy of reworking classics, for Spring/Summer 2027 he explained, “We wanted to go back to the archive and take our best items from the ‘90s, from the past, and remix them. We wanted to change the look but keep the DNA intact.” In addition to reconsidering the proportions, fit, fabric, and colors of Tommy classics like button-down shirts, polos, and cable knits, Hilfiger reintroduced his crest from the ‘80s and even referenced an iconic 1985 advertisement. The cheeky NYC billboard that positioned him as one of “The 4 Great American Designers for Men” at the start of his career returned in the form of a maxi dress. Color spoke volumes with primary hues of red, yellow, blue, and green, as dueling checks and stripes cohabited many of the looks. 

He also explained that he made most of the silhouettes oversized: “I think oversized is here to stay for a while because of the comfort factor and the fact that it’s a proportion a lot of young people like to wear.” The designer wasn’t kidding; some polo shirt sleeves reached past the elbows, shorts hems lingered below the knees, and a gigantic logo tote looked as if his flag had been snatched right from the HQ doors and converted into a bag. 

While referencing his past, there was an undeniably contemporary feel to Hilfiger’s latest “remix.” It’s the designer’s constant openness to the now that launched him into global recognition in the ‘90s and keeps him on the pulse today. As he reasserts his Big Apple roots in the 2020s, his runway show at The Plaza was a microcosm of the melting pot that New York has always been for him. While acknowledging a short lull in New York City after the 2020 pandemic, today he confidently says, “It’s back… It’s Brooklyn, it’s Soho, it’s the Lower East Side, it’s Chinatown, and then there’s the Upper East Side and the Upper West Side — it’s all just bustling.”

In this conversation ahead of Hilfiger’s SS27 runway show, the designer discussed the significance of The Plaza Hotel in his memory, how “fashiontainment” became his bread and butter, and the current evolution of his “classic American cool.”

Hypebeast: You’re returning home to The Plaza Hotel, where you once lived, and I want to ask when you resided there and what first attracted you to this iconic place?

Tommy Hilfiger: I lived there from 2007 to 2018. When I heard that they were dividing the Plaza into hotel and condos, I thought I would go look. They wouldn’t let you upstairs to see the apartments, but they had a model they could light up according to the floor and the apartment you wanted to see. They lit up the dome, and I said, “I like that.” But they said, “Well, I’m sorry, that’s the owner’s apartment.” And I said, “If he ever wants to sell it, let me know.” 

A couple of weeks later, I got a call. We bought it and were delivered a white box a year later, so we decorated it to our liking and moved in.

What significance do the Palm Court and Terrace Room hold for you as the venue?

That’s iconic New York. The location is great. It’s a location that I think is suitable for everyone. People come from downtown, they come from overseas, they come from uptown. They really congregate on 59th and 5th Avenue quite a bit. The interior, to me, is quite fabulous because of the architecture. I love the Palm Court. It reminds me of Casablanca, old world. And there’s something about it that has that charisma, that effect.

Given that the Plaza has hosted so many icons over the years, what kind of encounters did you experience while you lived there?

So many people pass through the doors, so you see a lot of different people. People coming from Hollywood, sports stars, music stars, families, all different kinds. I’ve seen a lot of people come and go.

Do you have a favorite memory of The Plaza?

I think it was when I brought my daughter to the Eloise shop. She didn’t want to leave.

How would you describe the mood or theme you’ve landed on for the latest collection?

We wanted to go back to the archive and take our best items from the ‘90s, from the past, and remix them. We wanted to change the look but keep the DNA intact. Then we decided to look at the proportions, the fit, the fabric, the colors, and the detail. So the remix was in motion. We brought the crest back from the ‘80s. We made most of the items oversized. We made some of the polos and rugby shirts shrink. If you can imagine a voluminous trouser with a shrunken top, that is sort of the mix.

I think oversized is here to stay for a while because of the comfort factor and the fact that it’s a proportion a lot of young people like to wear. So we want to give it to them in new fabrics, new colors, new details. We brought back our tartan plaid, sailing gear, rugby shirts, high-waisted pleated trousers with very wide legs. The idea is that there are no rules. You can really mix it up, and there’s a clash of color that’s happening. Preppy, classic American, remixed.

What influence has American prep had on the DNA of Tommy Hilfiger as a brand?

Everything. The backbone of the brand. I began designing it in 1984, and I was emptying my closet, looking at what I had been wearing in previous years. A lot of it was very preppy. I thought, why don’t I take this prep and remix it? Why don’t I make it oversized, make it relaxed, add new details, and make it really cool? And that’s how I started in 1985. When I launched it, it was very different. People were wondering, “What is this?” As time went on, we found that customers embraced it in a big way. They loved it. So then we started adding denim, women’s, children’s, a lot of colors, stripes, and different patterns. 

All of the rappers, hip-hop kids, athletes, preppies, surfers, skaters, and even the guys climbing in the Rocky Mountains with gear were wearing it. Then young women started wearing the men’s, too. At that time [in the ‘90s], we were really fusing fashion and music, and we made it our business to go out and find musicians to dress. So my brother, being a musician, knew a lot of people. He brought me Snoop Dogg, Britney Spears, and then Sheryl Crow popped into our offices one day. 

Your brand has been embraced in streetwear subculture since the late ‘80s and ‘90s. Did this surprise you at first? How has your relationship with streetwear evolved over the years?

What happened was my brother Andy said, “You have to hear this music,” and they were rapping about Tommy Hilfiger. I was like, “This is cool. This is very cool.” And these kids were very cool. We invited a lot of these music groups and rappers into our showroom, like Grand Puba, the Brand Nubians, and Sugarhill Gang. We would say, “What would you like?” And they would put it on and wear it out and go play in a venue that night. So all of a sudden it started spreading. 

One day my brother brought me this guy called Snoop Doggy Dog. I said, “Who?” And he said, “This is Snoop Doggy Dog.” So Snoop came into our showroom, and he looked around, saying, “I love that, I love that, I love that.” He wore one of the rugby shirts on Saturday Night Live and lit it up even more. I thought this was fantastic because I love music, I love musicians, I love the culture. I loved the idea that we could actually dress these people and then see them on stage or have them sing about it in the music. That moment in time was a game changer. 

Some people called it streetwear, and some people called it urban, but it was none of that. It was basically a remix of the classics and done in different ways. Suddenly, all of this unfolded into the luxury market, so we had a resurgence, and now we blend it all into everything we’re doing. We just call it classic American cool.

How does the energy of New York City continue to inspire you today?

It’s more energetic today than it was even back then. Something is happening; I don’t know what it is. It’s Brooklyn, it’s Soho, it’s the Lower East Side, it’s Chinatown, and then there’s the Upper East Side and the Upper West Side — it’s all just bustling. There was a moment a few years ago, I think during COVID, when everything slowed down. It was like, “Oh, New York’s not too cool anymore, not so much fun anymore,” but it’s back.