Men In Heels: The Most Iconic Moments Throughout History

From Louis XIV to Harry Styles.

Even though stilettos and platform-bearing shoes are now associated with feminine style, the high-heeled footwear was originally designed to be worn by men and men only. Over the course of history, the heels have traveled all over the globe and were ultimately worn by everyone from male soldiers to aristocrats and royals the world over.

Here at VMAN, we have gathered six of the most iconic moments from the history of high-heeled shoes in menswear — scroll down to see our top picks below:

King Louis XIV
When King Louis XIV reigned in France, his court has set the fashion for expressing political privilege through refined dress, particularly the elegant high-heeled shoe covered in red leather worn only by those with access to the court. The fashion soon spread to England, with King Charles II later portrayed wearing a pair of enormous red, French style heels during his coronation ceremony.

David Bowie

Heels were a staple for the funk and rock musicians of the late 20th century, and the rock’n’roll icon David Bowie was quickly picked up on the trend. Bowie was never afraid to take a risk — which made him famous for his wild onstage show looks. His shoes were almost as memorable as his music — everything from scrunched-up leather boots to shiny red platforms and leather kitten heels.


Prince was not only WEARING heels — he managed to do the splits, jump up, high kick, squat and run back and forth on stage with specially built 4-inch and 3 1/3-inch height boosters at his soles. The iconic musician was famously 5’3” and wore heeled shoes by choice, once saying that he liked to wear heels because women were more attracted to the elevated shoe — so why not?

Harry Styles

The looks that Harry Styles to 2019 Met Gala incited a lot of talk in the industry, making for another iconic ‘men in heels’ moment. The singer-songwriter turned heads on the red carpet when he paired a see-through black top and high-waisted pants with heeled black boots that had an almond-shaped toe — making history with this quintessentially androgynous look.

Jared Leto 

Most recently, the actor and musician Jared Leto flaunted a bold look that featured a pair of gold-heeled disco boots. Leto has very appropriately worn this gender-fluid look to Gucci’s Fall 2020 menswear show — wherein the collection itself challenged characteristics of masculinity in fashion.

Rick Owens

As part of his Fall/Winter 2020 menswear range, the American fashion designer has released a pair of five-inch heels with a chunky platform. Made from black leather, the sleek shoe was destined to become a head-turner that will go down in the history of menswear.

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