November 1997
Elliott (at the MTV Europe Music Awards) "wanted to be pleasing at the weight she was at," says mom Pat. Stylist June Ambrose says she dressed her so that "you saw her jacket instead of her shape."

September 2001
By the MTV VMAs four years later, "her body was slimming down, and she wanted things cut very precisely," says Ambrose. "Her jackets were shorter because her legs were slimmer."

August 2002
Elliott "went old-school '80s"for the VMAs, says Ambrose. "The track suits were slimming." Adds mom Pat: "Pink is her favorite color."

December 2002
At this photo shoot Elliott had her own baseball jersey customized with Swarovski crystals. "They have the most shine," says Ambrose. "She's taking an athletic look and making it more feminine."

July 2003
Elliott is queen of the remix in the music studio, and her look in the current Gap ad campaign with Madonna is similarly eclectic. "I cut up one of their zip-front hoodies and put it on the jean jacket," says Ambrose. "The T-shirt was an airbrushed mural of herself, and we had her pants grommeted, stoned and airbrushed again, which was important because of that old-school style." Through the years, adds Ambrose, Elliott "has gone from playful and hip-hop to sexy and soulful but still young and fun."