New York (CNN) -- Tommy Hilfiger began his career selling jeans out of the back seat of his car in upstate New York. On Sunday night, the designer celebrated the 25th anniversary of his fashion label with 25 limited-edition pieces inspired by American legends. 

"It's been an amazing journey from where I started," Hilfiger told CNN as looks derived from classic style icons hit the runway. 

"Grace Kelly--we have a halter dress inspired by her and a sleeveless trench, but with a modern twist," Hilfiger said. 

Next came a Steve McQueen-inspired navy pea coat, a James Dean-inspired leather motorcycle jacket and a Debbie Harry-inspired hooded sweater. 

Hilfiger said music, film and pop culture have always helped spark his ideas. In the early days, top rap musicians often sported his label. It symbolized cool street-wear in the 1980s and 1990s. 

Today's collection has evolved into a more preppy, country-club, classic look -- but with a rock 'n' roll vibe. 

"It's what I like to call the Tommy Twist," Hilfiger said, dressed in one of his own looks for the season: red trousers and a navy blue blazer, the epitome of relaxed preppy. 

In keeping with his pop-culture-infused style, the fashion show's after-party featured a live performance of critically acclaimed American rock band The Strokes, who made a comeback appearance after years of touring in Europe and Canada. 

After four years on hiatus while honing their skills on the music festival circuit overseas, the invite-only bash at the Metropolitan Opera House was the perfect opportunity to return home, said Denise Sullivan, a spokeswoman for Hilfiger and the band. 
what did Grace Kelly inspire?
 a halter dress