How do you do prep without being snobby? It seems like an impossible task, given how tied the style is to the British and American elites.

But Tommy Hilfiger has managed it – throughout his career – channelling the clean classicism and casual confidence of prep without ever veering into elitism. Hilfiger’s prep is open and inclusive, cool and current.

Case in point: his SS27 show, which, yes, featured modern prep poster girl Gigi Hadid, but also SoundCloud songstress Slayyyter, who treated us to live performances of “UNKNOWN LOVERZ” and “Dance...” – much to the bemusement of the largely middle-aged press, who had no idea who she was. Hilfiger, as usual, was ahead of the curve.

The following day, the American designer sat down with Dazed at the brand’s HQ on Fifth Avenue and shed light on the collection – inspired by the time he spent living at The Plaza, the landmark hotel and apartment building where the show was staged. He also discussed his approach to fashion more broadly, the foundations of which were laid in the 1980s, the heyday of New York’s art scene.

It was then that he met Andy Warhol, the figurehead of that scene, who was revolutionising how we think about not just art, but fashion, fame and celebrity. Warhol had a seismic impact on Hilfiger and, 30 years after his death, the advice he gave him is still at the front of his mind when he thinks about his business.

I really want to know about your connection to The Plaza.

Tommy Hilfiger: I lived there for ten years. I had the penthouse. If you’re standing on the street and you see the dome, that was my breakfast room. Off the bedroom, there’s a balcony overlooking Central Park. Oh my gosh, I’m sad I sold it.

Tommy Hilfiger: I sold it because we weren’t using it – we had a house in Connecticut and my son was going to school there, so we would commute from New York to Connecticut every day and not even use it. So I thought I would sell it, but now I regret it. I did sell it to a friend, though, and he invites me over all the time.

Tommy Hilfiger: It was a great time in my life. I bought it in 2007 and it took me a year to redo it.

So in 2008, we moved in, and wow. Seeing Central Park every day made me feel like we were in the midst of nature.

So we’d go to the park, we’d go to the zoo in the park, we’d go jogging in the park, and biking in the park. Great restaurants in the area.

Great shopping. I mean, Bergdorf is right there.

When my wife needed a pair of shoes, I’d just say, ‘Go to Bergdorf. You’ll get it all in a little bit.’ Or she would say, ‘I think I’m just going to take a walk,’ and then she’d come back with her bags [of shopping].

This collection – and your brand as a whole – is about American prep. How would you define American prep?

Tommy Hilfiger: American prep is all over the board. There are traditional American prep brands, and there are a couple of brands that are in the zeitgeist. But this is who we are as a brand, and it’s been our identity and personality for 40 years now. We haven’t gone minimalistic or decided to be something that we’re not. We’ve stayed on track.

When I designed the first line in 1984, for a 1985 launch, I took all of my preppy clothes out of my closet and I said, “OK, how do I change these?” The first thing I did was make them oversized. I added colour. I wanted preppy to be cool, and we broke through because there was nobody doing it. Nobody was doing it the way we were doing it.

“Travis Kelce is the man. He’s a very cool guy” – Tommy Hilfiger

Tommy Hilfiger: Gigi. Jisoo. A lot of the sports stars love it.

Tommy Hilfiger: Travis is the man. He’s a very cool guy and really a sweet, nice person.

Tommy Hilfiger: Well, our collaborations have been very successful. With Gigi, Zendaya, Shawn Mendes, and Lewis Hamilton… And we thought, ‘OK, how do we do it in a new way?’ And we hadn’t really done it with a big sports star to that extent. So we thought, ‘why not Travis?’ He’s like the all-American guy.

What’s your favourite thing about your job?

Tommy Hilfiger: Every day is different. Some days we’re looking at story and design. Other days we’re looking at models for the show. Other days we’re looking at locations for an ad campaign. I love the creative, but I also love the business. I like to really pay attention to what’s going on in the business.

That ability to straddle the creative and the business is obviously a reason behind your success.

Tommy Hilfiger: I think a lot of founders who are successful, like Mr Lauren and Mr Armani, have really focused on the business as well.

What would you credit as the secret behind your success creatively?

Tommy Hilfiger: That’s a good question. I always focus on what I think the customer wants to buy, but also I don’t want to look like another brand. So every time we come out with an item, I ask myself, does that look like Tommy Hilfiger?

I also like to think of how to market the brand, and I think we’ve done a great job connecting to what I call ‘FAMES’: fashion, art, music, entertainment, and sports. So I’m a very curious person, and I want to know what’s going on in pop culture.

Andy Warhol taught me a long time ago to surround yourself with celebrities, and he painted and photographed them. But we collaborate with them and put them in ad campaigns, and I think showing up with their fame.

Tommy Hilfiger: I met him in the early 80s; he invited me to his factory. There was filming going on in the basement, a band practising in another area, and a painting studio in another, where he was doing the silkscreens.

They were on the floor drying, so many of them, and he said, ‘Would you like one?’ I said, ‘Yeah, I’d love one,’ and he said, ‘Well, that one’s $2,000. This one, the Elvis, is $1,500.’ I said, ‘I can’t afford that.’ But as soon as I started becoming successful and making money, I started buying Warhol.

“[Andy told me] to surround yourself with celebrities... His Factory was a pop culture castle” – Tommy Hilfiger

Tommy Hilfiger: Yeah. I mean, I went to Studio 54 and Andy was there with Halston, Jerry Hall, Bianca Jagger, David Bowie. It was a crazy time.

What’s the biggest lesson that he gave you?

Tommy Hilfiger: To surround yourself with celebrities.

That’s so interesting. What was he like as a person?

Tommy Hilfiger: Reserved, quiet, quirky. But genius, a total genius.

You must have met so many interesting people through him.

Tommy Hilfiger: His Factory was a pop culture castle, with people coming in and out. I mean, I met the Ramones in his studio, the New York Dolls, Debbie Harry. The 80s was a very impactful time for me.

I mean, he laid the foundation for so much pop culture and for how we think about fame and celebrity now, right?

Tommy Hilfiger: Absolutely. Because it wasn’t just Hollywood stars he would want to engage with. It was athletes, writers, all sorts of creative and talented people.

Tommy Hilfiger: No, not at all. He would walk down the street with a stack of Interview magazines, handing them out to people.

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