Through July 4, The Post, in conjunction with the Milken Center for Advancing the American Dream, is featuring US citizens explaining what the American dream means to them in 2026 — including Tommy Hilfiger, founder and principal designer of his eponymous brand.
My parents really wanted me to go to college, but I had a problem — dyslexia, undiagnosed. I was getting poor grades because I couldn’t read, and I was embarrassed to tell anyone.
It was the mid-sixties and all the great music groups were becoming cultural icons. I wanted to be a rock star, so I bought a guitar, but I couldn’t play.
During the summer of 1969, my friend and I bought 20 pairs of jeans from New York City. We rented a shop in Elmira, New York, and called it People’s Place. The store did so well that we opened more locations on college campuses.
We overexpanded, and eventually our accountant said, “You owe a lot of money.” We filed [for] bankruptcy. It was embarrassing, but I knew I had a knack for designing clothes, so I started
designing for the companies we had been buying from. I had many starts and stops but I never took my eye off the dream. I could picture myself becoming successful.
I interviewed with Calvin Klein to be a designer, but the next day I met Mohan Murjani, who owned Gloria Vanderbilt. He told me, “We’ll build Tommy Hilfiger into your own brand and you’ll compete with Calvin Klein.”
So I designed a full collection. I put the clothes in suitcases, went into stores and asked to see the buyers. I got orders from Bloomingdale’s, Saks Fifth Avenue, and Macy’s.
I didn’t have money for advertising, so I started giving clothes to musicians. Pretty soon they were wearing my logo in cities around the world.
What started with music grew into deep connections across art, entertainment and sports, becoming a core part of the brand’s DNA. More than four decades later, that inspiration continues to position the brand at the intersection of fashion and popular culture.
The American Dream Video Project showcases real stories that illuminate pathways to opportunity. Featured at the Milken Center for Advancing the American Dream (MCAAD), this series is part of the Center’s celebration of America’s 250th anniversary. MCAAD is Washington, DC’s newest cultural institution, offering interactive exhibits and stories about achieving the American Dream. For more information, visit mcaad.org.