The Untold Fashion Story of Lil' Kim's Iconic Purple Pastie Jumpsuit From the 1999 MTV VMAs

When Lil’ Kim walked onto the MTV Music Video Awards red carpet in 1999, she had no idea that her iconic purple jumpsuit would cause even Diana Ross to absolutely lose it. When the two divas announced the VMA for best hip-hop video alongside Mary J. Blige, Diana just couldn’t resist jiggling Kim’s exposed breast, which was covered by a single lilac seashell-shaped pastie. If you’ve ever wondered what went into creating one of the most era-defining fashion moments of the ’90s, we spoke with Lil’ Kim’s stylist, Misa Hylton, who shared all the details ahead.

“I had no idea that Diana Ross was going to fondle her. That was a nerve-racking moment,” Misa said to POPSUGAR. Neither did Kim, who opened up about the incident in a 2002 interview: “A lot of people ask how did you feel, but honestly, I think she was just giving me a little motherly tap. Like, ‘Girl, do you know you have a boob hanging out?’ But she was real nice.” Misa used simple eyelash glue to secure the pastie to Kim’s breast, telling us she “didn’t overthink it” because she didn’t expect Diana to give Kim that loving jiggle.

Misa’s design for Lil’ Kim featured a one-sleeved jumpsuit made of an iridescent, sheer, lilac Indian bridal fabric with silver and purple seashells embroidered throughout. Misa added a bell sleeve, left one breast exposed, and covered Kim’s nipple with a seashell pastie cut out from the extra fabric. “I wanted to make something really ornate and feminine and pretty, to offset the fact that she had one breast out,” Misa explained. The glamorous, sexy outfit was complemented by a monochromatic lilac wig by Diane Alexander and silver glitter platform mules by Steve Madden.

Left: Nicki Minaj at Haider Ackermann Autumn/Winter 2017. Right: Miley Cyrus on Jimmy Kimmel Live, 2015. Image source: Getty

“Missy Elliott actually inspired the look,” Misa said. “We were hanging out one weekend and we were talking about fashion and Lil’ Kim, and she said, ‘You know what? If I was Kim, I would just say f*ck it and I would have one titty out.’ Because Kim could do some crazy sh*t like that. So I just said, wow, that would be kind of hot. So I saved the idea, and the next big event we had was the 1999 MTV Music Awards.”

Misa’s purple pastie look for Lil’ Kim is one of the most influential fashion moments of the early 21st century, because it changed what a woman rapper could look like. “Lil’ Kim came out showing a tit or two being like, ‘my femininity and my being female is an asset as opposed to a hindrance to overcome,'” said vintage clothing dealer and stylist Gabriel Held in The Remix: Hip Hop X Fashion.

Before Kim’s sensual, breast-flaunting display, women rappers were encouraged to hide their sexuality in order to be respected in the hypermasculine world of rap and hip-hop. Kim’s look not only introduced a new woman-rapper aesthetic in the ’90s that currently shapes the careers of Nicki Minaj, Cardi B, Megan Thee Stallion, and others, but her collaboration with Misa has also influenced a multitude of fashion imagery, from high-fashion houses like Saint Laurent to stars like Rihanna, along with standout street style moments.

Today, Misa’s iconic purple pastie jumpsuit for Lil’ Kim is archived in a top-secret location, but you can relive the beauty and glamour of that look in pictures from the 1999 MTV VMAs ahead.

Model Binx Walton walks the Saint Laurent Spring/Summer 2017 runway. Image source: Getty / Bertrand Guay