Brad Pitt's linen skirt on the Bullet Train red carpet has the internet abuzz, but looking back, the history of men in skirts dates back to 14th-century royalty.

Suits for men. Dresses and skirts for women. And no mixing interchangeably. That has been the standard for dress in western fashion as long as we've known it, or at least, how many people have been raised to belive it.
It wasn't until pop culture figures fromm David Bowie and Kurt Cobain to Harry Styles and, most recently, Brad Pitt began ssporting women's skirts without threat to their masculinity did people begin seeing men in dresses in a different light. Perhaps to the surprise of modern upholders of c ertain gender-specific constructs, men have been wearing dresses for centuries.

Ancient Romans

King Wiliam III

King Henry IV

Renaissance Dress

Ancient Romans wore draped togas. Men in the 14th century wore tights under skirts almost daily. European royalty were donned in ornate skirts and heavy makeup and wore these "feminine" silhouettes with pride. It wasn't until 19th-century dandy fashion, pioneered by fashionable English aristocrats, reimagined masculine style through the emphasis of suits.

David Bowie

Freddie Mercury

Kurt Cobain

Dennis Rodman

Moving into the 20th century, gender roles increased in rigidly for men's and women's dress. It would take creative trailblazers to experiment with women's clothes. Artists like androgynous icon David Bowie in the '70s, glam-tock singer Freddie Mercury in the '80s, and grunge rocker Kurt Cobain in the '90s, represented a free-spirited subculture where men could gender bend as they please. Another gender-bending figure, American basketball player Dennis Rodman, wore a full wedding dress for his wedding to himself in 1996.

Billy Porter

Young Thug

Harry Styles

Nowadays, men strutting in dresses is nothing new. Though it still may be controversial for some, the late 2010s and early 2020s have shown that clothing is genderless. With iconic fashion moments like Harry Styles' record-breaking Vogue cover (the magazine's first male cover star fronted the publication in a custom Gucci gown), Billy Porter's monumental Christian Siriano suit dress worn at the 2019 Oscars (and the many red carpet gowns to follow), and even Brad Pitt's recent grunge-y linen skirt moment, trends have proven that anyone can wear anything... and it doesn't have to be that revollutionary after all.

Men in Dresses: Fashion History

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