Grace Jones – 73

Jamaican model and actress Grace Jones has risen to popularity for her androgynous appearance as well as her progressive music. She has contributed greatly to the cross-dressing scenery and was looked up to by fellow stars like Annie Lennox all the way to Lady Gaga. She was a staple in the disco scene back in the 1970s. Her music career continued to flourish too.

Aside from that, Jones has also dabbled in acting. She was cast in several low-budget films from the 1970s to the 1980s until she was cast as Zula in Conan the Destroyer. She later appeared in A View to a Kill and Boomerang. She is still active in the music scene and has been collaborating with a variety of artists over the years. To her credit, Jones has made a significant impact in the cross-dressing as well as in the music industry.