The Visionary 2025: A 40-Year Journey With Tommy Hilfiger

From selling clothes from his car to creating a global brand, Tommy Hilfiger is a true fashion icon. His fireside chat with NRF President Matthew Shay didn't disappoint.

Image: Runway Magazine

On building the brand:

“I opened my first store with an investment of $150 and 20 pairs of jeans. So at that point, I thought, okay, well, I'll try this for a while and see how it goes. And I became obsessed with retail. And for 10 years, I ran my stores in upstate New York while dreaming about building my own brand. So 40 years ago this year, I started Tommy Hilfiger”

“And I started it with the thought that I would build a brand that would compete but not look like the competition. I wanted it to be different, and I wanted to keep it relevant and stay in the zeitgeist.

So I've connected with pop culture, what I call fame, fashion, art, music, entertainment and sports with celebrity and mainly musicians to keep the brand alive and out front”

On becoming a pioneer:

“Well, it was building a community. And I thought that catering to people who were interested in music and fashion would be my lane. I think that every business has to have some sort of definite focus. And that was my focus, and it still is today.

It's gone beyond just music and fashion because obviously it's sports and fashion, it's Hollywood and fashion. It's influencers with fashion and helps me carve out this journey to build this lifestyle, global brand”

On the role of music:

“Well, I always liked music and I thought that the rock stars who were coming to the US from England and coming to Woodstock and going on a tour looked very cool. And I like the way they were dressed.

And I like to figure out what might be next before the consumer knows what they want next.

Tommy Hilfiger

So I wanted to sell those types of clothes to my customers. So I would drive to New York City, four and a half hours away from my hometown of Elmira, and I would buy really cool clothes to take back to my shops and sell them.

But I called the stores people's place because I wanted the stores to be for the people and the people who were interested in music and fashion”

On celebrity:

“My philosophy was that if I were to dress the stars, their fans would come to us. And we started out dressing everyone from Britney Spears to Beyonce to Lenny Kravitz to, you know, David Bowie and Iman and the Rolling Stones.

And it became about fashion and entertainment. Then we did some movies with, you know, Hollywood stars. And then we started dressing sports stars and I thought that their fans would continue to come to us.

And then we started doing collaborations with various people like Gigi Hadid, Lewis Hamilton, Shawn Mendes, where we brought them into our design studio and allowed them to co design with us.

We gave them the opportunity to learn about passion from the inside and also co brand with us. And that has been, I would say, a phenomenon in and of itself that I never expected to be as big as it is.

And then we started doing see and buy now fashion shows, where instead of having fashion shows and delivering them clothes six, nine months later, I wanted the consumer to be able to be in the audience and click and buy whatever they would see on the Runway”

On disrupting:

“A shift is a game changer and a new journey, a new beginning without abandoning the past, because I think the past is really important.

We have a DNA and we have codes to the brand that we never want to abandon, but we want to modernise and evolve going forward. So that journey is always changing and always evolving and always moving forward.

We never want to become static or go backwards, we always want to move forward. And I think that's very important for all of us, including our team, to understand that we always have to look ahead.

And one of my favourite questions to my team is, what's next? Because if you don't know what is next, then maybe you become complacent or static. I like to figure out what might be next before the consumer knows what they want next”

On AI:

“25 years ago, people were saying that people will never buy clothes on the Internet or buy clothes via E commerce. And they said they'll never buy perfume or beauty or footwear. And we know how that works.

So I think AI is going to change everything. AI is going to propel businesses ahead and I think, you know, there's a danger in it also.

But I think that you, you have to stay abreast of what is going on, the tech world, because the tech world is going to be the horse that pulls the wagon. It is really shaping our lives and we have to be very well aware of what is going on and how it will benefit us”

On the Tommy Hilfiger legacy:

“Well, I would like the brand to last forever, to continue on, but I would also like to be known for having helped others, especially young talent, who may not find the opportunities that we could offer them just by introductions, by mentoring.

I would like to be known for a company and an organisation that has empathy, and we were very generous in terms of the charities we support, whether it's autism or breast cancer, Save the Children, we're very conscious of the environment.

We really believe in inclusivity and we're very diverse in our customer base as well, as well as our teams. I would like to be known for all of that”

On advice for others starting out:

“If you're a startup, pick a lane and stick with that lane. But do what you love. Really follow your heart and do what you absolutely love. But I would say that if you're a creative person, you should somehow find a partner who is a business person, because there are so many incredibly talented people out there who fail, because understanding the business of the business is just not in their wheelhouse.

So I think it's really important to surround yourself with the best possible people who can do what you're not great at. And I've always thought that I should surround myself with the best possible people in many different aspects, from legal to accounting to merchandising".

And I've always wanted to hire up, hire people who I think who are even smarter than I am and maybe have a different vision or could enhance the brand”

Tommy Hilfiger, a fashion icon.