Dressing Down Tommy Hilfiger

Mick Jagger was there that night in 1996, watching the cheering boys with dreadlocks and the girls in shirts embroidered with the enigmatic logo that Tommy Hilfiger created a decade before, when he was still a nobody. The rock star was among hundreds of people gathered in a tent near Lincoln Center to see Mr. Hilfiger, the charismatic clothier from Elmira, N.Y., receive the Menswear Designer of the Year award from the Council of Fashion Designers of America.

Back then, everything in the world seemed to be going Tommy's way. "There were these city kids, along on this magical ascent, because Tommy had crossed the barriers - he'd crossed both racial and demographic barriers," said Joseph Abboud, the clothing designer and a friend of Mr. Hilfiger, who was there that night. "Tommy had become the darling, he was at the pinnacle; he had transcended the whole preppy-Ivy League-Ralph Lauren-wannabe image to create a whole new paradigm of what the market looked like."

Driven in part by the association with hip-hop stars like Snoop Dogg and Coolio, Mr. Hilfiger's business boomed. And it is still huge: For its last fiscal year, the Tommy Hilfiger Corporation posted revenue of $1.9 billion, by selling mostly casual clothes throughout the world, and by licensing its name and red, white and blue logo for accessories like handbags, watch