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15 Celebs Who Broke Gender Norms in Fashion Way Before Harry Styles Did

The internet went wild after Vogue featured Harry Styles on their cover — all fancy, looking cute, and wearing a Gucci dress. While Harry, in fact, is the first man to grace the cover of Vogue, he certainly is not the first man to wear a dress. If ancient civilizations, like Ancient Egypt, are any indicator, men here rocked it in some type of a skirt — just like women did.

Bright Side loves to see guys and gals strolling down the street in their own unique ways, so we decided to introduce you to some people who redefined fashion for us.

1. David Bowie

David Bowie is famous for performing under the avatars of many different characters with a unique and often androgynous aesthetic. At a London concert in 1973, he performed as Ziggy Stardust in a short silk dress with an Asian-looking print. The print is said to be inspired by Stanley Kubrick’s A Clockwork Orange.

2. Marlene Dietrich

Marlene Dietrich, an actress from the 1920s and ’30s, regularly wore suits, which doesn’t seem like a big deal to us now. Yet, at that time, girls mostly wore pants only for outdoor activities and swimming, except for working class ladies. Dietrich helped people to see that women could wear pants in their everyday lives.

3. Katharine Hepburn

Katharine Hepburn is another revolutionary of suit-wearing from the 20th century. Along with Marlene Dietrich, Hepburn helped to shift the view of trousers on women from a garment of necessity into a garment of fashion. She also fancied men’s haircuts and makeup, typical for those times.

4. Prince

American musician Prince often dressed in colorful and bold outfits. For example, in 1984, he celebrated his birthday and the release of his album Purple Rain in a pink flowery onesie with fishnet sleeves.

5. Kurt Cobain

Kurt Cobain was a vocal feminist and sometimes changed out of his baggy cardigans and ripped jeans and into dresses. Along with other members of Nirvana, he sometimes performed and had several photoshoots in female clothing, proving he was man enough to wear a skirt. He was also featured wearing a dress on the cover of Face magazine. Nothing is more rock ’n’ roll than respecting women!

6. Elton John

Sir Elton John is a literal icon. Not even a fashion icon, just an icon. One can have a field day in his wardrobe of flashy, larger-than-life outfits, but for now, let’s appreciate him performing in a dress with, eh, whatever this headwear is.

7. Lil Nas X

American rapper Lil Nas X reinvented cowboy fashion in the 21st century. His palette of flamboyant western looks includes the brightest pink, lime, blue, red, and silver outfits. The man just can’t get enough of those colors!

8. Young Thug

In 2016, the mixtape Jeffery by rapper Young Thug featured him wearing a ruffled lavender dress and an Asian-inspired conical hat. The outfit was created by Italian designer Alessandro Trincone who is also well-known for challenging gender norms with his menswear.

9. Nico Tortorella

Actor Nico Tortorella explores their gender identity via fashion. So Nico can often be seen gracing the red carpet wearing dresses and colorful outfits.

10. Billy Porter

Actor Billy Porter has continued to stun Oscar attendees with his outfits for several years in a row. His fashion range is best embodied in his hybrid “tuxedo dress” (yep, it’s a thing), which symbolically includes elements of both classic male and female evening garments.

11. Michael Urie

Actor Michael Urie demolished the 2019 Met Gala with his half-and-half look. Half glittered suit and half pink tulle dress.

12. Chella Man

Chella Man is an internet personality, model, and artist, who tends to play with forms and exaggeration to express themselves.

13. Annie Lennox

Annie Lennox’s orange cropped hair and men’s business suit in the music video Sweet Dreams (Are Made of This), according to BBC, “broke the mold for female pop stars.” Her extraordinary, androgynous image was at odds with her contemporaries. Luckily, she never gave up her gender non-conformity: in her 60s she still rocks it (hah!) in suits and leather jackets.

14. Liberace

Władziu Valentino Liberace — or just Liberace — is an American pianist who donned extravagant costumes even decades before Elton John. Consider the sheer opulence — even borderline tackiness — of these looks!

15. Ezra Miller

Among other epithets, Ezra Miller’s fashion style was called “outrageous.” Whether it’s outrageous or not, it is bizarre for sure. Just a casual look for the 2019 Met Gala: a suit, a mask, lipstick, 7 eyes, and a — are those diamonds? — corset. Lovely. For the premiere of the first Fantastic Beasts movie, Ezra outright cosplayed Hedwig, the snowy owl. And it wasn’t even a themed event.

Bonus: Harry Styles himself

This man never disappoints: style is in his name.

How soon do you think it will be totally normal for men to wear skirts and dresses?

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