Lil’ Kim, 1999
Lil’ Kim’s mermaid-inspired purple jumpsuit, wig, and sequined pasty will go down in history as one of the most memorable MTV VMA red carpet looks. Lil’ Kim had no idea when she walked onto the MTV Music Video Awards red carpet in 1999 that her iconic purple jumpsuit would make even Diana Ross absolutely lose it.
Pamela Anderson, 1999
Pamela Anderson went for a bold look at the MTV Video Music Awards in 1999. The actress wore a white corset with sparkly, embellished pants and an equally embellished belt, all of which was topped off with a pale pink feathered hat because, well, why not?