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.
Photo: Courtesy of Tommy Hilfiger
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.)
