Roberto Cavalli ensemble, embroidered denim and printed silk crepe de chine, spring 2003, Italy, gift of Roberto Cavalli

Lil’ Kim has been known for her adventurous, designer-driven style since the mid-1990s. Working with stylist Misa Hylton, Kim pioneered a sexy, feminine style and acted as an ambassador between hip hop and high fashion brands like Roberto Cavalli, Versace, and Marc Jacobs. She wore a version of this 18th-century-inspired denim mini skirt ensemble to the Spike Video Game Awards in 2003.