Hilfiger opened his own store, The People’s Place, in 1985, and then went on to form his own company, Tommy Hilfiger. The brand went public in 1992, and a few years later, he started distributing women’s clothes. By 1997, he had opened his first store in Beverly Hills, Calif., and then another in London one year later.
Over the years, Hilfiger introduced women’s intimate apparel into the world and brought back the brand’s original style of “classic American cool.”
In 2006, Hilfiger sold Tommy Hilfiger Inc. to Apax Partners, a private investment company for $1.6 billion. Four years later, Apax sold the company to Phillips-Van Heusen for $3 billion.
Hilfiger — who is married to Dee Ocleppo — has also enjoyed other endeavors as well, including sponsoring Lenny Kravitz’s Freedom tour and Sheryl Crow’s If It Makes You Happy tour. He also hosted The Cut, a reality series on CBS, in which 16 designers competed to work for him. Hilfiger also appeared in several movies, including Zoolander and Ocean’s Eight, in addition to writing several books.
Recently, Hilfiger sold his 13,344-square-foot Greenwich, Conn., mansion for $45 million. The estate sits on 22 acres and has six bedrooms, seven bathrooms and three powder rooms.
This is the eighth house the couple has renovated and sold in the past 35 years. They originally purchased the home for $31.37 million in 2010. Now, the pair is looking to relocate to Palm Beach, Fla.
“I hear from my friends in real estate that the market is very strong, and it hasn’t been this strong in years,” he said about the new move.
The duo is in the process of selling their Miami home, and Hilfiger just sold his Plaza Hotel penthouse for $33.25 million in 2019, in addition to a Palm Beach mansion for $35 million in 2017.