Hosted by Highsnobiety’s Editorial Director Christopher Morency, “On the Record” is a podcast series of intimate, off the cuff conversations with icons and cultural engineers that have shaped the worlds of fashion, music, tech, art, business, sports and youth culture at large. For this episode, Morency spoke with legendary American fashion designer Tommy Hilfiger.

For almost 40 years, Tommy Hilfiger has changed how young people around the world dress. Pushing the boundaries of what a fashion business looks like commercially as a true global brand that just last year generated $4.7 billion dollars in revenue. In recent years, he's collaborated with Kith and Vetements.

Business aside, the storied American brand reshaped what, and especially who, drove influence among youth culture. He was a pioneer in seeing musicians, especially hip hop artists, as powerful marketing vehicles that could culturally, and financially, create value for the business.

First it was Grand Puba from hip hop band Brand Nubian, who shouted out the brand in a song with Mary J. Blige. Then came the rest. Britney Spears, Lenny Kravitz, Aaliyah, Destiny’s Child, Snoop Dogg the list goes on.

Remember, this was at a time when fashion brands refused to work with hip hop artist, dismissing them as drivers of youth culture, and believing a too close association with predominantly black artists would be brand dilution. How times have changed for the better.

I called up Tommy who during our call early on in lockdown was on his boat. We discussed it all, from the early days of Destiny’s Child and Aaliyah wearing the brand to why he's venturing outside of fashion, into tech, hospitality and media.

The below interview is a written version of ‘On the Record’ Season 2, Episode 8. It has been edited and condensed for clarity. The original interview was conducted in the beginning of the Covid 19 pandemic.

On the Meaning of Fashion Brands Today

When I started out in the fashion business, I always wanted to move beyond just being a fashion brand. I've always had the vision to become a pop culture purveyor and innovator in the world of F-A-M-E, the acronym for fashion, art, music, entertainment and sports. Because I think that in pop culture, fashion, art, music, entertainment and sports, you need to move the needle, make a difference in society and in the world of youth who are enamored with what’s going on in pop culture, whether it’s music oriented or connected to Hollywood or connected to maybe the tech world but whatever is really becoming influential in the world of pop culture is meaningful. [So] I've always wanted to surround my brand with pop culture, pop culture icons, pop culture movements and I continue to look forward and think very much that way.

On Merging Fashion with Sub Culture

In the late eighties, there was this phenomenon that was just beginning to surface. It was called Hip Hop. Hip Hop was really based on rap music and had never been exposed to the [mainstream] public, probably before 1988. The way [artists] formed, the way they dressed, their lyrics, their beats. In the mid eighties kids would walk down the streets of New York City with big boom boxes, pounding music. That was sort of the beginning of it. You would see a guy with a baseball hat backwards and an Adidas tracksuit about four sizes too big. It was just a different phenomenon that was beginning to take place. I was fortunate enough to be connected to the culture, and the Hip Hop kids at the time embraced my brand and viewed my brand as their designer brand.

Russell Simmons, who was starting his own brand, Phat Farm, said, "The reason these kids are really interested in your brand is because it makes them feel rich." Because in the very beginning, in 1985, when I started creating my brand, I created clothes for myself and I wanted my clothes to be preppy, but I wanted to be very cool. I didn't want them to be like Ralph Lauren or Brooks Brothers. I didn't want them to be too aristocratic looking or uptight. I washed everything. I made everything oversized. I made everything super, super casual and relaxed and they embraced my brand as their designer brand.

On Creating His Signature Aesthetic

In 1985, when I started creating my brand, I created clothes for myself and I wanted my clothes to be preppy, but I wanted to be very cool. I didn't want them to be like Ralph Lauren or Brooks Brothers. I didn't want them to be too aristocratic looking or uptight. [So] I washed everything and made everything oversized. I made everything super, super casual and relaxed and they embraced my brand as their designer brand.

On His Early Love for Musicians

Prior to starting Tommy Hilfiger, when I was 18 years old, I opened a jeans shop called People's Place. I sold bell bottom jeans, fringe vest, really cool hippy and rockstar type clothing. It was my dream to really be a musician myself, but I wasn't talented enough, so I decided to supply musicians with clothing. To dress a lot of different rock bands and performers, but at the same time, build my own cool clothing company. It was always based on my love for music and my love for rock style. I mean the kind of clothing that the groups were wearing in the sixties and in the seventies when I was a young teen, you couldn't find in stores. Jimi Hendrix would wear the most incredible jackets with bell-bottoms his girlfriend would sew for him. The Rolling Stones were dressing in women's clothes. David Bowie was creating Ziggy Stardust outfits, Led Zeppelin and the Who were looking more like British Mods. All of that influenced me so much.

On the Hip Hop World Embracing Him

I wanted to connect my brand to the music world, [so] when I was embraced by the Hip Hop community, it was like a dream come true. Then Hip Hop started becoming incredibly popular. Guys like Puff Daddy and Jay Z started jumping into the arena and Dr. Dre and Tupac and the West Coast Rappers. There was this whole phenomenon happening around me, and I was designing into it because I would listen to what they would want [and] they wanted everything way oversized. They wanted all the jackets, all the shirts logoed and very, very bright. They wanted their jeans five sizes too big. They wanted brand new sneakers to wear with their baggy jeans and backwards baseball caps. Then they started wearing big gold jewelry and gold chains. They really created this phenomenal style that was way ahead of the fashion world. What it made me think at the time was that in order to survive, evolve, reinvent, and build a lasting brand, I had to stay ahead of the curve in terms of what was going on in pop culture.

On Staying Ahead of the Curve

I started dressing women in men’s clothes. We dressed Aaliyah in our menswear with pants too big, boy's underwear, broad tops made out of underwear. Then I met this music group when they were in their early teens. They performed for me during my fashion shows. They were called Destiny's Child. The lead singer was a girl by the name of Beyonce who also wanted to dress like a boy with Tommy logos. Within underground culture, it was embraced but it certainly wasn’t mainstream. After we ran advertising in magazines with photographs of Aaliyah wearing it, young women from all walks of life were asking for it. They would see it on Salt-N-Pepa, TLC, Missy Elliott. Female urban musicians. It was accepted and that led me to doing really cool clothes for women. But all of this taught me to stay ahead of the game and to stay very connected to music and pop culture.

On Disrupting the Traditional Fashion Calendar

I’d been doing fashion shows for over 20 some years and I thought they were antiquated. I thought just having editors and buyers in the audience and closing it off to the public was an antiquated idea. I didn't think it was new or modern. I knew hundreds of thousands and millions of people wanted to come to see fashion shows. I thought this was really antiquated anyway that they would have to wait six months to get the clothes into the stores after everybody sees photographs of the celebrities already wearing the clothes during the show. I thought I should reinvent it and really create something brand new. So I wanted to invite the public. I wanted them to have a memorable experience. I wanted to be very democratic and I wanted to really change the rules. [So] I had to figure out how to change the design calendar and the manufacturing so I would have the products available during the show. And that took quite a while to re-adjust, but it’s worked. It's been very successful. I think a lot of people will probably attempt to do it in the future, but not many people were successful in attempting to do it because of the logistics involved.

On Honing His Design Signature

I love the fact that we years ago established a look, a feel to the brand that is standing with us today. We are, if you close your eyes and you think of a Tommy Hilfiger brand, whether it's a pair of headphones or a pair of sneakers, you see red, white, and blue. Years ago when Nike took the name off the swoosh, I think it was in '86. I thought, okay, Phil Knight is a genius. He just took the name of his company off his logo and people know what his logo stands for [today]. I had that dream to do that at some point in time.I did it about, I think, 10 years ago when I felt that most people knew that the red, white and blue flag is. I believe in brand identity in a big way, regardless of what you're selling or producing. I always think it can evolve and I always think it can change and be reinvented. Whereas I think a lot of people don't think about those things because they think that the company name is the company name and they're going to make a certain product line and stay within those confines.

Working With Celebrities as Co-Creators

Well, this all sort of happened while we were thinking of developing the see-now-buy-now fashion show extravaganza. I thought, why are we designing all of these products when in fact, some of these young people like Gigi [Hadid] who was on our runway has a sense of style that’s very cool and relevant, and she could actually influence us? I asked her to co-design with me and we did the Tommy x Gigi collections that were incredibly successful. It wasn't just having Gigi Hadid as the face of the brand, but as the creative influencer of the brand. Then we did the same with Lewis [Hamilton] and the same with Zendaya. I don't want to do what was. I want to do what is next. I really believe that a lot of it has to do with a digital experience. A lot of it has to do with the type of shopping experience that is modern and new, as opposed to, I don't know, just going into a store or going on a website, looking at still images. I really believe it's going to change. I want to be ahead of that change.

On Expanding the Brand

We’re going forward in a new way. The livestream shopping [platform] we’re creating is really allowing us to build our own broadcast channel through social media. We really believe that getting in front of the consumer in a unique way and a modern way is the best way. I'm [also] looking at new technologies. I'm looking at the digital world and figuring out how it connects with our world. I really believe that media and entertainment are such an enormous part of our lives today. I cannot stress how important it is. I want to be a fashion media entertainment brand. I don't want to be just a fashion brand. I think being just a fashion brand is very limiting and somewhat boring even. That’s exactly why I’m reaching beyond just fashion. So we’ll go beyond just being a fashion brand. We're developing products that are connected to one's lifestyle like electronics, headphones, chargers, gadgets, hotels, residences, experiences, health, and wellness. I like what's going on in Hollywood, Silicon Valley, in the VR world. [I want to] collide all of this together and come up with our own product ranges that are outside of fashion.

It's a risk. I think that a lot of fashion brands run by large corporations are afraid of risk. I also think that many brands might not have the vision to do it and might be afraid to do it. Many of them are somewhat myopic in my estimation. Many fashion brands are antiquated. They wouldn't really think of doing some of the things we do and that's okay. I do believe that many brands will try figuring out how to do see-now-buy-now going forward, but not every brand. I think that you always have to find your lane and once you find your niche, you have to expand upon it and you have to build a better mousetrap than your competition.