90's Gender Bending Fashion Was To Die For

Gender bending fashion is having a moment in fashion right now, and I couldn't be more excited to see designers and celebs flaunting arbitrary gender roles. Although it feels new and fashion-forward, people have been playing with this concept for decades. Each era is informed by a different cultural landscape, and I'm partial to gender bending fashion of the '90s. Why? It was the era welcomed grunge and punk into the picture, which completely changed the way people approached dressing outside their gender.

The '80s deserve major credit for setting the scene for lads in dresses and ladies in suits to flourish in the '90s. This is the era when "masculine" fashion went mainstream: as women entered the workforce in droves and the economy soared, power suits flooded the market, the New York Times points out. The infamous '80s staple mimicked men's business suits with sharp lines and shoulder pads (oh, the shoulder pads). The intended effect was for women to appear more traditionally masculine, and therefore be taken more seriously in the workplace (ugh).

While gender-bending fashion was nothing new by the time the '90s arrived in a screeching of guitars and flannel, it was a decade that saw significant changes in the way the public dressed. Amanda Marcotte over at Slate attributes the rising popularity of flannel to the Seattle music scene, home of the late and great Kurt Cobain. "The decidedly feminist bent of the scene resulted in a wave of gender play in street fashion," she writes. "Men picked up painting their fingernails, and let's not forget how Kurt Cobain wore dresses in public, and skirts on men popped up on runways as a result. Better remembered is the playful way women's grunge fashion dealt with gender. Let's not forget the baby doll dress/combat boots combination."

As far as big stars go, the early '90s followed a similar pattern in gender bending as the late '80s, with big acts such as Annie Lennox continuing to court the androgynous style that made her famous. But it didn't take too long before grunge's influence caused a disturbance in the force. Gender bending fashion became less about dressing wholly as another gender and more about picking and choosing elements to incorporate into a look — such as a male singer performing in a corset (looking at you, Marilyn Manson), especially as the '90s progressed. This decade also brought drag into the mainstream with RuPaul and MAC's legendary 1994 Viva Glam campaign.

Ready to check out some ladies in suits and gents in dresses? Scroll down for the best gender bending moments in '90s fashion.

1. RuPaul

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Drag queen RuPaul became a drag superstar in 1994, when the performer starred in MAC's first Viva Glam campaign.

2. Grace Jones

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Grace Jones may have debuted her legendary style in the '80s, but she rocked her androgynous look well into the '90s.

3. Annie Lenox

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Major shoulder pad fan here: Lennox was famous for performing in oversized suits.

4. Boy George

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Boy George was never afraid to go for the glam in the '80s, and that didn't change in the '90s.

5. Marilyn Manson

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Manson accessorized many of his looks in the mid-to-late '90s with feminine accessories, such as this corset.

6. K.D. Lang

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In addition to her musical talents, Kathryn Dawn Lang is pretty much the poster child of gender-bending fashion, a suit aficionado among the ranks of Annie Lennox.

7. Dennis Rodman

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Professional basketball player Dennis Rodman at a book signing for his autobiography in a wedding dress. While the stunt seemed inexplicable at first, it was later revealed that the designer of the dress paid him $10 million to wear it.

8. Kurt Cobain

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In addition to playing with gender norms on stage, Kurt Cobain advocated gay rights and identified as a feminist. His quotes are just as relevant today as they were two decades ago.

9. Annie Lenox In Camo

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I think we can all agree that Annie Lennox carried off even the late '90s camo trend.

10. Prince

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Early '90s Prince was still played with gender norms in his performances. Observe: this 1992 example, which features a heeled boot and a jacket with feminine tailoring.

11. Marilyn Manson With A Garter Belt

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Now for Keeping Up With Marilyn Manson: the performer circa 1997, in a garter belt.

12. RuPaul & Kurt Cobain

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Yep, that's RuPaul behind Kurt Cobain, who is sporting a set of sunglasses that wouldn't have looked out of place on Twiggy. Thank you for bringing us this jem, 1993 MTV Music Awards.

13. Eddie Izzard

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Seen here in 1996, Eddie Izzard's makeup game (and jokes) have been on point for more than two decades.

14. Joan Jett

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Style icon for rocker girls everywhere, Joan Jett performs in her signature androgynous look: black, black, and converses.

15. K.D. Lang In A Striped Suit

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K.D Lang killing a 70's inspired suit... in 1990.

16. Prince On Stage

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Prince performs in another suit with feminine tailoring.

17. Annie Lennox Rocking Plaid

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Annie Lennox is queen in head-to-toe plaid.

18. Sinead O'Conner

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Ever the rebel, Sinead O'Conner told Huffington Post she shaved her head in an act of rebellion against her producers' wishes.

19. Sinead O'Connor In All-Black

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O'Conner would often perform in androgynous outfits such as this so the audience would focus on her voice. Did it work? You betcha.

20. Kylie Minogue

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Kylie Minogue paid homage to the King of Rock at the Smash Hits Poll Winners Party after-party (say that five times fast) in 1992.

21. Eddie Izzard's Eyeliner

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Even Eddie Izzard embraced grungy liner in the late '90s.

22. Madonna

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Ever the fan of flouting expectations, Madonna debuted this menswear-inspired suit at a performance in 1990. It was a surprisingly demure look from the singer... until she tore it off to expose her iconic cone bra underneath.

23. Jean Paul Gaultier


It turns out man-skirts aren't new after all: Jean Paul Gaultier first sent men's skirts down the runway in 1984. Here, a model walks a striped, pleated version down the runway in 1994.

24. Dave Navarro

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Jane's Addiction frontman Dave Navarro was a major proponent of guyliner. He was also known to paint his nails.

25. Kathleen Hanna

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Kathleen Hanna of riot grrrl band Bikini Kill takes a feminine ensemble to another level with twelve-pack printed on her T-shirt. And yep — that's Joan Jett to her left. On that note...

26. Joan Jett

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Joan Jett sticks to her awesome androgynous greasier-than-thou look in this 1994 performance.

Images: Getty Images