Home Life 20 celebrities who challenged gender norms

20 celebrities who challenged gender norms


20 celebrities who challenged gender norms

Are you tired of regressive, repressive gender norms? So is Hollywood! From gender-bending red-carpet looks to candid discussions about toxic masculinity, it’s heartening to see these 20 stars rejecting gender expectations.

Billy Porter

Billy Porter has never let toxic masculinity keep him from working a red carpet. Along with his undeniably strong fashion sense, Porter has refused to let gender define his acting career, notably playing a genderless Fairy Godmother in Amazon Prime’s recent Cinderella adaptation.

Porter has also been outspoken about the fact that Black and LGBTQ+ artists who challenge gender norms are often given less recognition and praise than their white, straight peers.

Miley Cyrus

Whether she’s letting her underarm hair grow out or taking after her father by rocking a mullet, it’s clear that Miley Cyrus has no time for gender roles. In fact, the former Disney star has been incredibly honest about her gender fluidity, stating that gender has “nothing to do with any parts of [her].”

Jennifer Aniston

It’s no secret that women—especially those over 30—face immense pressure to have children. As an A-list star without children, Jennifer Aniston has been the victim of public scrutiny for decades, prompting her to pen an essay in 2016, reminding the tabloid media that her personal decisions are none of their business.

It’s a heartening reminder that challenging gender roles goes beyond fashion, and that women do not need to tolerate judgment for their personal choices.

Marlene Dietrich

Although more stars are rejecting gendered fashion than ever before, the concept is far from new. Marlene Dietrich was an in-demand star from the silent film era to the 1970s, and was noted for her androgynous fashion taste.

She was pulling off menswear long before it was socially embraced, and helped pave the way for future generations of women in Hollywood.

Janelle Monáe

Janelle Monáe is nothing if not versatile. Not only does she balance film roles with her music career, she’s known for bouncing from androgynous pantsuits to feminine gowns on the red carpet.

Monáe has also been candid about her gender identity, sharing that Prince’s outlook on gender resonates with her and she is alright with people using whichever pronouns they would like when referring to her.

David Bowie

Let’s be honest: it wouldn’t be fair to discuss gender-bending artists without mentioning Ziggy Stardust himself.

There’s so much to be said about David Bowie’s gender transgressions that even scholars have jumped in, with one suggesting that, through his personas and performativity, Bowie had become the “king of drag.”

Jonathan Van Ness

JVN is one of Hollywood’s most outspoken LGBTQ+ voices, and he has been refreshingly candid about his relationship with gender.

Although he still uses masculine pronouns, he has come out publicly as non-binary and gender-nonconforming, and has opened up about how liberating it is embracing his femme side.

Billie Eilish

An undeniable truth is that our society sexualizes young women, especially those in the spotlight. When Billie Eilish skyrocketed to fame as a teenager, she fought back against attempts to comment on her body by wearing baggy clothes.

Now, Billie has donned more traditionally feminine looks on red carpets and magazine covers, while also returning to her signature baggy style every once in a while.

Annie Lennox

Male musicians are more often praised for genderbending, but women in the industry have been doing this for decades as well.

One half of the iconic pop duo Eurythmics, Annie Lennox has weighed in on her androgynous style on stage, discussing how it represented equality in her professional partnership with Dave Stewart, as well as the greater fight for women’s equality.

Ruby Rose

From the moment audiences saw her in her breakout role on Orange Is the New Black, Ruby Rose and her androgynous look have drawn a lot of attention.

The gender-fluid star once struggled with bullies for not conforming to gender roles, but is now an LGBTQ+ advocate that seeks to help young people embrace their true identity.

Elton John

If you were asked to describe Elton John’s stage persona in one word, chances are “flamboyant” would come to mind.

In his own words, drag has been a “lifelong love affair” for the music legend, who has carved a name for himself not only through his talent, but also through his over-the-top, often feminine stage looks.

Troye Sivan

A young and openly gay pop star, Troye Sivan is known for embracing makeup, feminine clothing, and emotional vulnerability. However, he has also been open about how intimidating it can be for men to embrace their effeminate side, and how he is still learning to be comfortable breaking gender norms.

It’s a good reminder that challenging gender expectations is an ongoing process, and it’s okay to work your way out of your comfort zone slowly.

Megan Rapinoe

Megan Rapinoe is a soccer star known for her talent on the field, brightly coloured hair, and refusal to be silent about the things she believes in. This includes her disdain towards “harmful gender norms and labels and binaries,” which she’s discussed while promoting her partnership with a gender-neutral deodorant company.

Robert Smith

Known for his eccentric hair and thick eyeliner, The Cure frontman has also used music as a medium to explore his relationship with vulnerability and gender norms. One of the most pervasive and dangerous messages associated with toxic masculinity is the idea that boys and men shouldn’t cry or express emotions.

Through the powerful track “Boys Don’t Cry,” Smith has challenged this notion and become a role model for embracing vulnerability.

Diane Keaton

Many Hollywood actresses will don a pantsuit at a movie premiere every once in a while, but no one is as committed to stripping gendered labels from formalwear as Diane Keaton. Her love of high-waisted pants and elegant suit jackets can be dated back to at least the 1970s, and has made her a laid-back, gender-nonconforming style icon.

Sam Smith

Sam Smith refuses to let the bigots define their Grammy- and Oscar-winning career. When they came out as non-binary in 2019, it sparked a backlash from trolls who refused to adjust to their new gender-neutral pronouns (they/them). However, Smith has not let the criticism stop them, stating in June 2019 they had “never felt this proud to be queer.”

Lil Nas X

With elements of rap, country, and pop, Lil Nas X’s musical style as well as his fashion style are certainly gender-bending. While he is still a relative newcomer to the music industry, there are countless examples of him challenging gender norms, from donning dresses at award shows to exploring his sexuality in his debut album, Montero.

Demi Lovato

Demi Lovato has always been an incredibly candid pop star, and that has not changed since they came out as non-binary in 2021.

On their podcast 4D, Demi has discussed how their recent haircut was an intentional move to distance themselves from gender expectations, and in an interview admitted they spent years living in a “hyper feminine state” to avoid bullying. Now, Demi has shed the internalized gender norms holding them back from their true identity, and advocates for the LGBTQ+ community.

Harry Styles

Harry Styles made Vogue history in 2020 as the magazine’s first solo male cover star—and he did it wearing a dress, no less.

Styles has a long history of wearing feminine clothing (and defending this decision publicly), stating that he’s very nonchalant about his sexuality and fashion taste, and is generally unbothered by labels.


Last but certainly not least, Prince was a gender-bending icon. His aesthetic as a performer was often feminine (and glittery!), and his lyrics were full of affirming messages to the LGBTQ+ community.

His music will always be a huge part of his legacy, but so will his liberating perspective on gender, which helped many men—especially Black men—embrace their own femininity.