Who

Fashion entrepreneur Tommy Hilfiger's company has seen better days, but the clothing line that bears his name soldiers on.

Backstory

One of nine kids raised in a strict Irish Catholic family, Hilfiger grew up in Elmira, NY and worked as a salesman at a Cape Cod boutique as a teenager. He was 17 when he pooled together $150 with two other high school seniors and opened People's Place, a hippie store in Elmira that sold jeans, records, and rolling papers. By the mid-70s, the store had seven stores in upstate New York, but following the recession at the end of the decade, the chain went bust. Tommy moved to the city, where he picked up work as a freelance designer and was introduced to Mohan Murnani, the entrepreneur who controlled licenses for everything from Gloria Vanderbilt jeans to Coca-Cola clothing. In 1984, the two launched Tommy Hilfiger, with Murnani supplying financial backing and Hilfiger articulating his "vision" to a team of designers. Hilfiger and partner Joel Horowitz later bought back the company and watched it take off like a rocket in the early 1990s as both jocks and rappers bought into the look—appropriations of the American flag and red-white-and-blue sportswear that mimicked the preppy casual wear that Ralph Lauren had patented a decade earlier. Before long, Tommy's name appeared on everything from bedding to perfume.

Those halcyon days have long passed. But Hilfiger doesn't have to worry much about his company's declining profits. He sold his stake when Apax Partners, the private equity firm co-founded by Alan Patricof, bought the company in 2006 for $1.6 billion. Tommy remains principal designer, and signs off on the creations of the brand's design team. For that arduous task he's remunerated with $14.5 million a year.

Of note

Hilfiger signed a dizzying number of licensing deals in the 1990s, a strategy that backfired when many of the company's products landed in the discount bin at low-end department stores. A cautionary tale about the perils of relinquishing control of your brand, Tommy Hilfiger (the company) never quite recovered from the blow and was forced to close several of its flagship stores by the end of the decade. Hilfiger's designers have since tried to restore the brand's image with a series of identity changes—from hip hop to high fashion to teenage trendy to all-American and everywhere in between. But a series of limp attention-seeking tactics (a Hilfiger-designed Game Boy, sponsoring a Britney Spears tour and competitive sailing yacht) failed to make much of an impact, and in a sign that the company has given up on the idea of a full-fledged Hilfiger comeback, in October 2007 it inked an arrangement with Macy's, under which the retailer would be the exclusive sales outlet of Tommy Hilfiger products.

Drama

Hilfiger has long elicited resentment among his fashion peers, mainly because he positioned himself as an industry titan long before he'd paid his dues. A 1986 Times Square billboard for the brand called Hilfiger one of the "4 Great American Designers for Men," alongside Ralph Lauren, Calvin Klein, and Perry Ellis; Klein later lashed out publicly against the ad's creator, George Lois. In more recent years, Hilfiger has been slammed as a lowbrow copycat and mass-market hack. The anti-Hilfiger sentiment peaked in the '90s when the company was involved in a messy lawsuit over sweatshop labor and a particularly nasty urban legend got off the ground that Hilfiger had appeared on Oprah and said, "If I knew that blacks and Asians were going to wear my clothes, I would have never designed them."

On screen

Hilfiger made an ill-fated bid for reality stardom in 2005. Much like his clothing line, Hilfiger's CBS show was a shameless knockoff, an imitation of Project Runway called The Cut. It lasted a season before its cancellation. Before that, he made several appearances on his daughter's MTV show Rich Girls.

Personal

Hilfiger split from his wife, Susie, in 2000. He has four kids from the marriage: Ally, Rich, Elizabeth, and Kathleen. He was engaged to Dee Ocleppo, a former model, in 2008, but the couple later called off their engagement. Hilfiger lives in an 18,000-square-foot Georgian-style house in Greenwich, which he purchased for $18 million in 2005, and owns a pied-a-terre at the newly-converted Plaza. He also has homes on the islands of Nantucket and Mustique. He sold his house on Further Lane in the Hamptons for $26.5 million in 2007.