My First Job in Fashion: Tommy Hilfiger

My first job in fashion was when I was 13 years old. I was working as a stock boy in a sporting goods shop in my hometown Elmira, New York. We sold football jerseys, basketball jerseys, all the equipment, and it was all made with such high-quality materials. I was obsessed.

When I was 18, I worked in another boutique in Cape Cod for a summer, selling rock and roll posters, incense candles, jewelry, and things like that. It was 1969 — the summer of Woodstock — and I was fascinated by musicians. I loved the way they dressed and I loved the way they would appear on-stage with hippie-style outfits.

In those early days at stores, I learned the customer is the judge, always. In fact, when  you’re working in a store on the selling floor, you learn a lot. Certain colors will never ever sell. Certain kinds of fabrics never do well, because of the drape or the hand feel. Fit is incredibly important. You can have the best-looking designs in the world, but if they don’t fit right, you don’t sell them. These were lessons from my early days in retail that I still think about today.

Around the same time, I also worked nights at a gas station. And from my jobs I eventually saved $150, drove to New York City, bought 20 pairs of bell-bottom jeans on the streets, and took them back to Elmira. I started selling them to my friends and opened a shop called People’s Place.

As well as the jeans, we were selling fringe vests, candles, incense, rock and roll posters, all sorts of cool gear at the time, but focused mainly on fashion, and while I was buying from the streets of New York City, and a lot of vendors, I kept thinking, “Wow, if I could design some of this, it would be really cool, because I would add a pocket here, I would make it a little bit higher waisted, maybe I would change the sleeves on a jacket.”

In the years that followed, I opened 10 People’s Place stores on college campuses all across New York state, from Cornell to Cortland State University. We became a favorite for young people who were fashion-conscious, but couldn’t afford to buy luxury. (Though as an aside, at that time, brands like Gucci and Louis Vuitton only sold leather goods.)

Tommy Hilfiger outside of People’s Place in his hometown of Elmira, New York.

I kept having ideas of how I would redesign the collections that I was buying for my stores, and at one point I said, “OK, I really want to build my own brand.” I was 19 at the time, and I kept picturing what it would look like. I would sketch rough ideas, it was like a movie in my mind, this dream that if I could build my own brand, I would do it in a certain way. I wanted it to be cool and preppy, but on-trend. And I wanted it to be wearable and affordable and accessible. I started designing pieces for my own stores. And found that a lot of the young people coming from college campuses were intrigued by the; they loved what I was selling and what I was designing.

When I was 25, my accountant informed me People's Place was in financial trouble. After eight years, I experienced bankruptcy in 1977. Looking back, that was a good experience. I wasn't really a business person early on, but that early bankruptcy taught me to really pay attention to the business part of the fashion business. It was a great education.

So in 1979, I sold my stores, moved to New York City, and started working in design for various companies to try to learn the craft. I didn’t know how to obtain all the fabrics and manufacture [clothes] in a professional way. So I worked for Jordache and learned how they were making jeans, and then, in 1984 I met the man who owned Gloria Vanderbilt jeans, Mohan Murjani. I had just interviewed with Calvin Klein to design Calvin Klein jeans and casual, and I had decided to take the job. But I had a meeting with Mr. Murjani the next day, and he said, “Why are you going to work for Calvin Klein? You should launch a brand that will compete with Calvin Klein.” I told him that was my ultimate dream, but I wasn’t sure I was ready. He said, “No, I think you’re ready. Let’s just do it.” So he backed me. He became my business partner and we launched my brand in 1985.

Tommy Hilfiger poses with his designs in his studio, New York, September 10, 1987.

Shortly after, we were thinking about doing advertising, but didn’t have a lot of money. My idea was to photograph some models in the Hamptons wearing the clothes. But then I met an advertising genius by the name of George Lois. I told him my idea and he said I was crazy. “It’ll take years before anybody even knows your name or really cares about the clothes,” he said. So I replied, “OK, what would you do?” A couple of days later, he came back to my office with storyboards, and he showed me an ad campaign called The Hangman, comparing my brand to Calvin Klein, Ralph Lauren, and Perry Ellis, by presenting a hangman puzzle spelling out all of our last names.

It blew my mind. I was like, “You can’t do this, you can’t compare me to other designers who have been around for decades. I’m a nobody, and I’m just starting out. How could you possibly do that?” He said, “Look, if you want the name to be known, and if you want people to even pay attention to what you’re doing. You have to do something disruptive.” He convinced me that if we were to run this ad, it would turn heads and it would create a buzz around the brand. And so we did a billboard in Times Square with the hangman campaign, and the press went crazy, the fashion world went crazy, saying “Who is this? Who does he think he is? How could he compare himself to Calvin, Ralph, or Perry?”

Tommy Hilfiger "The 4 Great American Designers for Men" advertisement T-shirt.

People hated me, and thought I was just completely arrogant and out of my mind. That was the one time I thought, well, maybe I should leave the business and do something else. But then I thought, if I really work hard and focus on making the clothes great, maybe I could get over this trauma of being so disliked.

So I went to work on the clothes. The quality, the fit, the detail. Around this time, Studio 54 was just about at the end of its era, and there was a new trend going on, inspired by ’80s music, like Michael Jackson and Madonna, who were both touring and wearing very cool clothes on-stage. It was inspirational. I wanted to make preppy clothes cool, inspired by musicians. So I made them oversized and relaxed. I added a lot of detail. I thought if I dressed musicians, their fans would come to my brand. My brother Andy is a musician, and he introduced me to a lot of different artists who started wearing mythe clothes.

Later, in the ’90s, musicians, like Mary J. Blige, even included Tommy Hilfiger in their lyrics. And the hip-hop kids on the street loved the clothes, so they became like walking, talking billboards for the brand.

Andy Hilfiger and Aaliyah during Tommy Hilfiger Fall 2000 Fashion Show and Britney Spears and Tommy Hilfiger, 1999.

But it was Snoop Dogg on Saturday Night Live wearing our Tommy Hilfiger logo rugby shirt in 1994 that really lit our look on fire. Oversized, relaxed, big logos. Up until that point, you wouldn’t see a lot of big logos on clothes. My team colors are red, white, and blue, as you may know, and we were doing like most of the clothes in red, white, and blue with big logos, which became advertising billboards for us, so that really positioned us into the culture in a very significant way.

A few years later, Britney Spears was just coming onto the scene, and she was our first Tommy girl. We were shooting her for the Tommy Girl jeans campaign the day her song “Baby One More Time” went to number one on the charts. Then, Aaliyah became a big, big star and was the star of our ad campaign, too, with Mark Ronson. We also sponsored Sheryl Crow’s If It Makes You Happy tour in 1997, and the Rolling Stones on their American tour in 1999.

After that, I went back to my roots of loving sports and authentic sport jerseys and clothing — in the sports store age 13 — and we did hockey jerseys, basketball jerseys, baseball jerseys, football jerseys, all sorts of sports-inspired rugby shirts and oversized jerseys to be worn with Tommy jeans or carpenter jeans, baggy jeans showing the underwear waistband, sailing jackets, all sorts of color-blocking, and we set this trend that continues to cycle. It was very big in the ’90s, and then it quieted down and became very big again 2012 onward. It never really goes out of style, but it shows up at different times.