WHEN did Tommy Hilfiger become cool again? Once a preppy kingpin and then a megabrand designer of urban streetwear, with over $1.9 billion in sales of baggy jeans and colorful logo jerseys in the United States at his peak, Mr. Hilfiger, in the 1990s, was very cool. But then, about 10 years ago, he just wasn’t. People became more interested in his divorce and his dating life and his daughter’s reality television show than his clothes, all of which looked increasingly like the result of a designer who was trying too hard. The situation had become so bad for Mr. Hilfiger that just a few years ago the company seriously considered selling his clothes at Wal-Mart. Magazines had stopped paying much attention to him. As had his customers — sales in department stores had dropped by as much as 75 percent. – From NY Times