Before Harry Styles, there was 14th-century royalty.

Suits for men. Dresses for women. And no mixing interchangeably. That has been the standard for dress in western fashion as long as we&rsquo;ve known it, or at least, how many people have been raised to believe it.
It wasn&rsquo;t until pop culture figures from <a href="https://www.lofficielusa.com/fashion/david-bowie-style-2021-fashion-makeup-trends" target="_blank" rel="noopener">David Bowie</a> to <a href="https://www.lofficielusa.com/fashion/kurt-cobain-90s-grunge-style-impact" target="_blank" rel="noopener">Kurt Cobain</a> to <a href="https://www.lofficielusa.com/fashion/harry-styles-best-fashion-moments-albums-songs-music" target="_blank" rel="noopener">Harry Styles</a> began sporting women&rsquo;s dresses without threat to their masculinity did people begin seeing men in dresses in a different light. Perhaps to the surprise of modern upholders of certain gender-specific constructs, men have been wearing dresses for centuries.&nbsp;

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 &ldquo;feminine&rdquo; silhouettes with pride. It wasn&rsquo;t until 19th-century dandy fashion, pioneered by fashionable English aristocrats, reimagined masculine style through the emphasis of suits.&nbsp;

David Bowie

Freddie Mercury

Kurt Cobain

Dennis Rodman

Moving into the 20th century, gender roles increased in rigidity for men's and women's dress. It would take creative trailblazers to experiment with women's clothes. Artists like androgynous icon <a href="https://www.lofficielusa.com/fashion/david-bowie-built-a-legacy-on-marrying-music-with-fashion" target="_blank" rel="noopener">David Bowie</a> in the '70s, glam-rock singer <a href="https://www.lofficielusa.com/film-tv/freddie-mercury-last-words-queen-documentary" target="_blank" rel="noopener">Freddie Mercury</a> in the '80s, and <a href="https://www.lofficielusa.com/fashion/marc-jacobs-brings-back-his-infamous-grunge-collection" target="_blank" rel="noopener">grunge</a> rocker <a href="https://www.lofficielusa.com/fashion/kurt-cobain-90s-grunge-style-impact" target="_blank" rel="noopener">Kurt Cobain</a> 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.&nbsp;

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 <a href="https://www.lofficielusa.com/pop-culture/alexandria-ocasio-cortez-defends-harry-styles-vogue-cover-dress" target="_blank" rel="noopener">Harry Styles' record-breaking Vogue</a> cover (the magazine's first male cover star fronted the publication in a custom Gucci gown) and <a href="https://www.lofficielusa.com/film-tv/billy-porter-stuns-in-every-color-2019" target="_blank" rel="noopener">Billy Porter</a>'s monumental <a href="https://www.lofficielusa.com/travel-living/christian-siriano-furniture-collection-1st-dibs-interview" target="_blank" rel="noopener">Christian Siriano</a> suit dress worn at the 2019 <a href="https://www.lofficielusa.com/film-tv/best-makeup-and-hairstyling-nominees-2022-oscars" target="_blank" rel="noopener">Oscars</a> (and the many red carpet gowns to follow), trends have proven that anyone can wear anything...and it doesn't have to be that revolutionary after all.&nbsp;

Men in Dresses: a Fashion History

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