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It Took Just One of Lil’ Kim’s Breasts to Change Fashion

With an assist from Diana Ross, at the 1999 MTV Music Awards, the hip-hop legend transformed the pastie from a cover-all to a sartorial centerpiece

Big naturals are more than just a body part. They’re an energy, a culture, a lens through which we consume and create the world around us. And while big-breastedness may be both spiritual and bodily, there is a material world and timeline of events that document how this culture came to be. As MEL’s resident boob culture writer and a woman of breast-experience, I’ll be analyzing these objects and happenings, telling the stories of their origins and their impact on society. This is Big Moments in Big Naturals.

Will Smith’s Oscars slap of Chris Rock notwithstanding, it’s typically the MTV Video Music Awards that provide the most frequent viral moments with lasting cultural relevance, like Kanye’s interruption of Taylor Swift, Britney Spears and Madonna’s iconic lip-lock or Lady Gaga’s unforgettable raw meat dress. It was at the VMAs, too, that breast fashion culture was forever transformed by Lil’ Kim’s left boob and Diana Ross jiggle of it. 

To be more specific, at the 1999 VMAs, 25-year-old Lil’ Kim wore a bedazzled lilac jumpsuit and a wig of the same shade. The outfit would have been a hit regardless, but one detail cemented its fame: The jumpsuit was strategically cut to leave the entirety of her left breast and arm bare. To keep the look safe for television, she covered her nipple with a sparkly, shell-shaped pastie. 

As Kristin Corry wrote for VICE in 2019, this sartorial choice ensured that Kim “didn’t just turn heads — she made the world remember her name. The look, styled by Misa Hylton, propelled the Hard Core rapper into global stardom, where she spent the rest of her career pushing the limits of how sexy a woman could be in hip hop.” 

Notably, the outfit wasn’t just sexy, but playful and creative, too. In fact, Kim looked downright cute, which only further highlighted the aggressive tone and lyricism of her music. With one tit out, Lil’ Kim proved that each of these characteristics could exist harmoniously — she could be hot, fun, sweet, angsty and serious all at once.

What further cemented her look in history, though, was the fact that Diana Ross touched her breast while on stage during the ceremony. Beforehand, Kim and Mary J. Blige stood at the podium, announcing that Ross would be coming out to present the next award. The moment Ross reached the duo, she placed her hand underneath Kim’s exposed breast and gave it a little double tap. (In 2013, Kim said that she interpreted it as a friendly way of saying, “Oh my god, you look sexy, girl, but do you know you have a boob hanging out?”)

Undoubtedly, Kim set the tone for breast and pastie fashion ever since. Just like Madonna with her conical bra, Kim transformed the pastie into a legitimate article of clothing, rather than a mere undergarment. The pastie was no longer merely a tool to hide a nipple — it was a way to underline it, to make it the focal point of a whole look. Artists like Nicki Minaj, Miley Cyrus, Rihanna and even Cher have all since worn similar outfits, proving the one-titty-out look to be almost as iconic as the woman behind it.