Moviefan2k4;4297282 said:
The main reason he wore heavy makeup had nothing to do with sex or gender; it was to conceal his vitiligo. Karen Faye said he tried hiding it from her too, at the beginning...but in a relatively short timespan, it became much more difficult to use the brown areas of his skin as a starting point. As a result, she used the lighter areas, which eventually took over the majority of his body. I remember Jermaine saying in his book, that Michael's chest looked like a white man with a coffee stain, from the disease.
His vitiligo skin disease was certainly not the main reason.
Michael Jackson was fascinated with applying heavy make-up on his face, mainly for creating that androgynous image that would make people speculate all the time about him.
On one occasion in 1986, Michael Jackson entered secretly Diana Ross’ dressing room (at the Caesars Palace in Las Vegas) and he started putting on her make-up.
Diana Ross was shocked to see that when she returned back to her dressing room.
That incident at the Caesars Palace also shows that Michael Jackson wanted to have androgynous (if not feminine) characteristics on his face.
Look also at his choice of colours of his make-up, which generally was a glossy, bright red lipstick tied with black (semi-) permanent eyeliner.
He chose those two colours because he wanted to create that chromatic antithesis on his face, which would in turn draw even more attention to him.
His androgynous look (in terms of make-up) became even closer to feminine in the ‘90s when he started to use heavier eyeliner and heavier mascara.
Keep in mind also that he used to treat his face like a piece of art.
After all, he was also a male pop singer, and it is very common for male pop singers to use heavy make-up on their faces with the intent to create an androgynous image.