Tommy Hilfiger Talks His Controversial Billboard, Snoop Dogg and American Idol

Photo courtesy of Joyce Culver for 92Y

Tommy Talk: Mr. Hilfiger with Fern Mallis.

From his first basement business to his new role on American Idol, Tommy Hilfiger has built a worldwide brand from nothing more than some thrift-store jeans and a strong dose of good old-fashioned hard work.

On March 8, Tommy Hilfiger sat down with industry insider Fern Mallis at the 92nd Street Y in New York City for a conversation on his life and work—from his upstate New York upbringing to the iconic American sportswear brand he founded.

Growing up in Elmira, New York, Tommy was the oldest boy of 8 brothers and sisters, all of whom continue to remain very close. "I was dyslexic but didn't realize it so my teachers and parents thought I just wasn't smart. I had to be creative and find different ways to learn, to finish my homework and to read a book," Hilfiger said.

"In high school, I wanted to be a football player but I was 5'3" and 90 lbs," Hilfiger laughed. Instead, Tommy and his buddies started their own fashion business. "We drove down to New York City and bought jeans and hippie clothes on the streets or from vendors in the West Village and we packed them all into this Volkswagen and drove it back up to Elmira," Hilfiger reminisced. Tommy and his friends would buy the jeans for $4. Then he would stonewash, cut and embellish them and then resell them for $12.

Hilfiger, who shocked his parents by telling them he wasn't going to college, opened his first store, called The People's Place, in a basement in Elmira.  "We burned incense and sold the jeans and all of our friends came. It was great!" Tommy followed the success of The People's Place by opening similar stores on college campuses, including Cornell.

When Tommy was 25 years old, his business went bankrupt. "Studio 54 had just opened in New York City and we were there all the time, instead of at the store."

Hilfiger then started freelancing and opened up a couple of other small businesses, which didn't last. He never went to design school, but admitted he never wanted to. "I wanted to generate the ideas and then have other people execute [them]."

The designer's first big break came when he befriended Perry Ellis. "I was freelancing at a textile company that was near his office and one Sunday we needed a spool of thread and I knocked on his door," Hilfiger explained. Shortly after, Ellis offered Tommy a job, which was followed by another job offer from Calvin Klein.

Hilfiger turned them both down and in 1984, he founded the Tommy Hilfiger Corporation, with financial backing from Mohan Murjani of The Murjani Group. Murjani was looking for a young designer to launch a new line of men's sportswear and met his match with Tommy.

As part of Tommy Hilfiger's first ad campaign, a billboard was erected in Times Square reading, 'The Four Great American Designers,' and listed only the initials R.L. for Ralph Lauren, P.E. for Perry Ellis, C.K. for Calvin Klein, and T.H for Tommy Hilfiger. At this point, Hilfiger was an unknown and the ad created quite the buzz, including some negative feedback from people in the industry. Hilfiger said, "That was the only time in my career I thought about giving up, but I decided to just work very hard and deliver."

In 1994, Hilfiger dressed Snoop Dogg for Saturday Night Live; the rapper wore an oversize T-shirt bearing the Tommy name. "We were creating a brand new trend of big logos, looser clothes and bold colors. It was preppy with a twist. We also caught the wave of casualization of the workplace and we were designing button-ups that were the right blend of luxe and sophisticated but casual," said Hilfiger.

Snoop wasn't the only celeb to sport Tommy attire. Artists like Britney Spears and The Rolling Stones followed suit by wearing Tommy on stage. "I have a saying," said Tommy. "FAME. F for Fashion, A for Art, M for Music and E for Entertainment. Using FAME as a marketing tool, I looked at iconic America and Americans for ideas and music was the core of it. The theory was that if the brand was dressing artists, then their fans would follow."

His newest role as the image advisor on American Idol will have him counseling contestants on what to wear. "If you look at any big star, you will notice they are also a fashion icon. If you have the talent, you need the full package in order to make it," said Hilfiger.

Hilfiger, who admitted he doesn't regret much of anything and views each failure as a learning experience, said he vows never to make the same mistake twice. In terms of the future, Hilfiger told the audience, "If I'm standing next to Armani, Karl and Ralph, I'm in the right crowd."

"The Mt. Rushmore of fashion indeed," Mallis quipped.