Jennifer Lopez, 2000
Jennifer Lopez knows how to put together a look that will go viral—and while there are a plethora of looks that come to mind, perhaps one of her most famous MTV VMA looks is the one she wore to the 2000s award ceremony with her then-boyfriend, Diddy. She may no longer wear Sean John—or date him for that matter—but her abs haven’t changed much in twenty years.
Jennifer Lopez, 2000
Macy Gray, 2001
It was the dress that was seen all over the world. Macy Gray, who is known for her outlandish style and music, decided to turn her award show dress into a walking billboard. “That was totally Macy’s idea, I just had to execute it,” says Ambrose, the designer of Macy’s immortal dress. “Working with Macy Gray was so much fun because she was an anomaly,” Ambrose remembers.
Macy Gray, 2001
