Just as society grew accustomed to women adopting trousers and shirts, defying traditional norms, men are now stepping up to surprise—and perhaps shock—audiences with their unconventional appearances.
Consider Billy Porter's memorable appearance at the 2019 Academy Awards, where he walked the red carpet in a stunning tuxedo dress by Christian Siriano, prompting headlines worldwide.
Billy Porter at the 2019 Oscars, photo credit: frenchly.us
But Porter wasn't the first to embrace this trend. The idea of men dressing in women's clothing has deep roots. In Shakespeare's era, women were banned from the stage, so male actors played female roles in costume. Similarly, in ancient Greece, Rome, and Japanese theater, men often portrayed women.
By the 19th century, the term "transvestite" emerged, describing men who wore women's attire. In Victorian England, the movement gained momentum with Ernest Bolton and Frederick Pak, who donned dresses and jewelry to stroll through London streets. They called themselves Fanny and Stella during these outings, causing public outrage and leading to city hearings.
Ernest Bolton and Frederick Pak, known as Fanny and Stella
Next came the flamboyant actor and singer Morris Young, who shocked early 20th-century audiences by declaring himself a woman rather than a man.
This trend, puzzling to many but fascinating to fans, was later embraced by global celebrities. You might be surprised who's on the list.
Male Stars in Dresses: A Look at Brad Pitt and Others Who Dared
David Bowie
David Bowie performing in bold attire
The legendary David Bowie lit up stages in vivid outfits, heavy makeup, styled hair, dresses, skirts, and high heels. The more shocking his look, the greater the public reaction—and the more memorable his performances became.
Mick Jagger
Mick Jagger in an extravagant stage outfit
This singer also embraced flamboyant fashion, especially early in his career, wearing neo-romantic dresses for performances.
Matt Stone and Trey Parker
Matt Stone and Trey Parker in comedic attire
Brad Pitt
And then came the climax: Brad Pitt, the sex symbol and heartthrob of millions. What drove this epitome of masculine beauty to take such a step?
It happened in 1999, when Pitt was young and knew how to create buzz. Rolling Stone magazine published a photo shoot that caused a sensation. The October issue featured Pitt in mini dresses and women's jewelry.
Brad Pitt's controversial Rolling Stone photo shoot
The shoot took place at a salt lake.
The concept was the brainchild of photographer Mark Seliger, inspired by a paparazzi scandal.
Pitt, tired of intrusive photographers, supported Seliger's idea:
"They constantly invade our lives, hoping to catch something juicy—how we blow our noses, or adjust our swim trunks on the beach," Pitt said sarcastically.
Pitt chose the dresses and accessories himself. Seliger's goal was to present the star in an unexpectedly striking way.
The public was shocked, and the project became legendary. Yet the paparazzi continue to snoop into Pitt's life as before.
Pitt himself described the unconventional photo shoot as an act of self-irony, with no deeper meaning.
Brad Pitt's self-ironic fashion statement
Marc Jacobs
Marc Jacobs in a bold fashion choice
As a renowned fashion designer, Jacobs constantly experiments with style. No one is surprised when he appears at shows in skirts. One memorable moment was his public appearance in a black sheer dress and buckled boots.
Iggy Pop
Iggy Pop modeling for Lady Dior
The rebellious singer stated there's nothing shameful about wearing women's clothing. He participated in a Lady Dior bag campaign dressed as a woman.
"I feel no shame when dressing as a woman. Because there's nothing shameful about being a woman," Pop said.
What are your thoughts on this?
