Another memorable VMAs fashion moment comes from Kim, who attended the 1999 show wearing a purple one-sleeved jumpsuit exposing one breast, which had on it a seashell pastie. "I wanted to make something really ornate and feminine and pretty, to offset the fact that she had one breast out," Kim's stylist, Misa Hylton, previously told POPSUGAR. She also revealed Missy Elliott had inspired the idea and encouraged Kim to make a bold statement.
What's also remembered about the evening is the moment when Kim joined Diana Ross and Mary J. Blige on stage to present the award for best hip-hop video. It was then that Ross famously jiggled Kim's breast. Kim later referred to it as a "motherly tap" in an interview with Carson Daly.