What Tommy Hilfiger Learned From Going Broke in the 1970s

a Message from NEAL

A hundred and fifty dollars, a long drive, and a gamble on bell bottom jeans that was mostly guesswork. Figuring out what we are meant to do is rarely a straight line—it might lead us either to sell hippie clothing and incense, or to dress rock stars for their concerts, or both. Tommy Hilfiger’s story shows that much of it comes down to throwing ourselves into a series of adventures in new adulthood and continually acting upon the valuable lessons learned from them.

Wishing you fulfillment,

From Selling Jeans to Teenagers to Dressing Rock Stars

“It was difficult for me because I was searching for the answer for so long, and the answer was right in front of me,” said fashion designer Tommy Hilfiger of his early years, “Do what I do best.” As a 17-year-old in upstate New York in 1969, Hilfiger took $150 he had earned at a gas station and made the 4-hour round trip drive to New York City. There he purchased 20 pairs of bell-bottom jeans which he sold out of the trunk of his car.

When this first adventure turned a profit, Hilfiger opened a hippie clothing shop, called the People’s Place, in the basement of a shoe store and began selling clothes, shirts, jackets, candles, and incense. The store was a hit and Hilfiger opened 6 more on college campuses, and he began designing some of the items: “Designing made me happier than anything I’d ever done,” he said, “I knew from that early work that designing would be my life.”

Unfortunately, due to the retail slump of 1977, Hilfiger went bankrupt and lost all his stores. He studied commerce so that in the future he would know both the business and creative side of the fashion industry. Hilfiger also did design work in New York City for Perry Ellis and Calvin Klein. And he spent time in India at the clothing factories, watching as his sketches were turned into clothes, which was excellent training for a designer. Indian textile tycoon Mohan Murjani approached Hilfiger about starting his own clothing line, and the Tommy Hilfiger Corporation was launched in 1985. Hilfiger’s preppy and collegiate staples were a hit, particularly as men needed clothes for “casual Friday” wear, and the company went public in 1992.

Hilfiger then pioneered a new marketing strategy in the mid-1990s. He sponsored musical events and tours for Michael Jackson, Britney Spears, the Rolling Stones, and others, and he launched a fragrance with Beyoncé. Additionally, the oversized versions of his clothes with giant logos he made for hip-hop performers exploded in popularity when Snoop Dogg wore a Hilfiger rugby shirt on Saturday Night Live.

As the 1990s ended Hilfiger’s sales plummeted in the U.S. He would eventually have to take the company private and make his clothes more exclusive again. But that is another story for another LIFEPATH Newsletter!

“It was difficult for me because I was searching for the answer for so long, and the answer was right in front of me.”

— Tommy Hilfiger

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