Prev 36 of 85 Next
36. Lil' Kim, 1998
A blonde Lil' Kim went sans pants to the 1998 Grammys, and opted for shimmery tights instead. The rapper was a massive fan of leotards, and would don a different version of this look for many red carpets to come. Thanks to her adventurous aesthetic, Lil' Kim was renowned in the fashion world, and was a favorite among designers like Chanel and Giorgio Armani.

Kim created many of these looks with her famous stylist, Misa Hylton. In the '90s, Hylton was known as the head stylist in the Hip Hop world, and worked with big names like Foxy Brown, Missy Elliott, and Mary J. Blige. "We weren't thinking! We were just doing," Hylton told Complex about working with Kim. "When you saw us wearing things, they were our own. There was no such thing as pulls and studio services that we’re able to do now."

During those years Hylton had to buy her clients' outfits with her own credit card because luxury labels wouldn't return her calls — hip hop wasn't embraced by the fashion community yet.

Because of that, Hylton and Kim would create many of the rapper's outfits — whether for the red carpet or for the stage — using pieces from their own wardrobes. "When it was time to do a music video, Kim would bring along her belts, I'd bring all my shoes. I would bring my fur, she would bring her fur. Un would bring his wife's jewelry. That's how we made it happen. It was all very authentic, and all those pieces were our own," Hylton explained. "When you saw us wearing things, they were our own. There was no such thing as pulls and studio services that we're able to do now. Those weren't options for us in the beginning."

So the outfit you'r seeing here could very well be pieced together with looks from her friends' wardrobes!