Cross-Dressing in the Music Industry: Then and Now

In 2016 it’s not hard to notice that the discussion of breaking down binary gender ideas is still going strong.

Our society and media is finally in a place where the idea of gender fluidity is taken seriously and noticed, as proven by the likes of Jaden Smith, Ruby Rose and Miley Cyrus. However the idea of removing gender boundaries has been around for a long time and was particularly prominent during the 1980s.

Here is a look at some of the fabulous androgynous icons of the 80s, and today’s musicians that they have inspired that continue to tell us today that there is no need to conform to or label yourself as one gender.

David Bowie


The news of Bowie’s death was hard to swallow for all of us. To millions, he was a pioneer of not only music, but blurring the social expectations and narratives of masculinity and gender. For that, we are eternally grateful. Bowie refused to stick to a formula, adding expression and rebellion in each song he created, show he performed and word he said. Bowie performed under several different personas and pseudonyms. He wore extravagant, form-fitting costumes and played overtly sexual music and defined glam. Bright hair and loud outfits, Bowie’s dub of Ziggy Stardust was a leap for gender fluidity in the music industry. For combining a wide array of non-standard identities, we salute you. Rest in power, sir.

Grace Jones


“Feeling like a woman, looking like a man…”

Grace Jones is widely considered as responsible for starting the cross-dressing movement of the 1980s. This is particularly evident in her iconic 1981 album cover for Nightclubbing, which depicts Jones in a masculine Armani jacket with a cigarette in her mouth- a product aimed predominantly at men until the “Torches of Freedom” marketing campaign in 1929. The angular padded clothing and flattop haircut would go on to become highly popular amongst black men throughout the 1980s. The ability to influence men and women alike in their fashion choices makes Jones a true pioneer in the breaking down of gender boundaries.

Annie Lennox


“I love to be individual, to step beyond gender”

Annie Lennox, a Scottish singer and one half of synthpop duo Eurythmics was inspired by Grace Jones and continued the cross-dressing movement throughout the 80s. She has inspired many of today’s musicians including Lady Gaga and Elly Jackson. Her wearing of suits and short orange hair became an iconic look in 80s pop culture. Lennox is widely considered a gay and feminist icon for her LGBT, HIV and feminist activism, something she continues to this day making bold statements as she challenges the depictions of women in modern pop culture.

Boy George


“I wear makeup and dress this way because I think it makes me look good. I am not doing it to make people stare at me. If I wanted to do that I could just put a pot on my head, wear a wedding dress, and run screaming down the street.”

Along with Annie Lennox, Boy George is considered another 80s gay icon. His unique and colourful public image was a true sign that men could rock makeup in a fashion predominantly associated with women. Boy George took inspiration from both male and female fashion and wore it in his own way and as a result became one of the most unique looking and vibrant artists of the 1980s. Boy George is currently a coach on the voice alongside Paloma Faith, and Ricky Wilson.

Elly Jackson


“I don’t have a sexuality. I don’t feel like I’m female or male. I don’t belong to the gay or straight society, if there is such a thing.”

Looking into today’s music scene it’s known that Elly Jackson professionally known as La Roux refuses to confine herself to one gender or even sexuality itself. She very often shows this through clothing as she rocks masculine suits, taking inspiration from Annie Lennox, and is well known for her signature quiff. Her sophomore record Trouble in Paradise was released in 2014.



“I guess all of us have a little bit of both, masculinity and femininity, and bridging the gap between those two things is really fertile.”

Arca is one of the hottest producers in today’s music scene, known for his work on the latest LPs from Björk, FKA twigs and Kanye West. Through his debut LP Xen released in 2014, he explored his feminine spirit and he explores this further through his fashion. His wearing of skirts and heels truly breaks down gender for him personally and for his fans. His second record Mutant was released late last year.



“To those who keep asking, I have no gender, no sexuality, and no fucks to give.”

Shamir is one of the freshest faces in the music industry today. His debut LP Ratchet soon became a critics’ favourite making several end-of-year lists. On top of his contribution to 2015’s musical output, his public image and statements regarding gender make him one of the newest role models in breaking down gender roles in fashion and identity. Through clothing, hairstyles and the wearing of nail varnish, which other male artists such as Troye Sivan have caught onto; he rips apart the construct of gender and sexuality and refuses to conform to the binary expectations of such a construct.

Words – Sandy McKenzie

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