Top 12 most iconic gender-benders of all-time

Top 12 most iconic gender-benders of all-time

Clothes don’t have a gender. The misconception that boys should wear blue and girls should wear pink is a social construct that has evolved over centuries. Pre-colonialism, many indigenous cultures recognized two-spirited people, who had both masculine and feminine energies. Just look at traditional attire and you’ll see that both men and women adorn interesting patterns, colours, materials with gender-bending attributes.

In the modern world, we have seen how fashion has contributed to the oppressive ideas around gender in society. It is hard to believe that women weren’t allowed to wear pants until the mid-20th century.

In pop culture, the tide turned after the 1960s and we saw more and more entertainers pioneering the gender-fluid movement. Here are our top 10 gender-bending style icons.


  1. Grace Jones

Grace Jones is the inspiration behind so many pop star’s iconic looks including Bjork, Lady Gaga and Beyoncé. She has proven not only to be a force within music but a fashion icon as well. Ever since the days of studio 54, the singer/songwriter/model/actress has always blurred the lines of masculine and feminine. Her style and work with Jean-Paul Goude defined the landscape of the 70s and 80s. It’s no wonder she is considered one of the most intriguing legends in musical history.


  1. Prince

The OG gender-bending hitmaker was always unapologetic about his fashion expression. One of the most famous male artists to don high heels, flamboyant costumes and overly sexualized outfits, Prince became the go-to person for gender expression in fashion in the 70s and 80s.


  1. Michael Jackson

You cannot have a gender-bending list and not include the King of Pop Michael Jackson. Over four decades Michael Jackson provided the world with iconic styles like the beaded white glove, red biker leather jacket and white socks. He always presented a cool, royal sense of androgynous style that will be worn for generations to come.


  1. Freddie Mercury

One of the best vocalists of our time, Freddie Mercury, opened new avenues for queer people in music through his extravagant outfits, unapologetic sense of self and quirky style. Whether he donned tight-fitting jeans and vest or colourful jumpsuits, Mercury always left a lasting impression at all his appearances. His influence on fashion can be felt even today.


  1. Ru Paul

The queen of drag has had an interesting fashion evolution in the world of entertainment. First spotted with a punk attitude in the 80s, Ru Paul became the supermodel of the world with an ever-changing fashion palette for the gawds. Mama Ru still stuns on the runway of her hit show “Drag Race” and proves that style really is forever.


  1. Somizi

South African queer icon Somizi always leaves tongues wagging when he dresses up. From fun hairstyles, top of the range fashion labels and his drag alter ego, Madam Gigi, Somizi holds his own in the gender-bending world of fashion and deserves a spot amongst the best of the best.


  1. Tilda Swinton

Oscar-winning actress Tilda Swinton has maintained her cool, avant-garde and androgynous style throughout her successful career. She’s a muse for so many designers and pioneered an understated yet cool sense of fashion. Her androgynous style has inspired so many up-and-coming designers from all over the world.


  1. Little Richard

The late music star Little Richard is one of the original pioneers of gender-fluid fashion. He was one of the first to unapologetically express himself when it was highly frowned upon for men to wear glittery clothes and make-up. Before David Bowie, there was Little Richard and that says it all.


  1. David Bowie

Whether you know him as Bowie, or Ziggy Stardust or perhaps the Thin White Duke, David Bowie left an indelible mark on fashion history with his outlook on glam rock. He broke the boundaries of music and fashion blending the femme and the masculine meticulously in his style. Though in the later years he stuck to wearing tailored suits but will always be remembered as a gender-fluid fashion icon.


  1. Boy George

Boy George is known for his soulful voice and his androgynous style of the 1970s and 1980s. The singer-songwriter and DJ has stood firmly at the top of gender-fluid style icons of the English New Romantic movement.


  1. Annie Lennox

“Short hair, don’t care” describes androgynous entertainer Annie Lennox who shot to fame with her pop duo, Eurythmics. As much as their hit songs got them a lot of attention, it was Annie Lennox’s cool and chic style that kept fans wanting more and more. She’s considered as one of the world’s greatest singers, but her style is certainly up there for disturbing the male gaze of the 1980s.


  1. Billy Porter

Billy Porter took the fashion world by storm in the past couple of years breaking every stereotype of what a Hollywood actor should look like. This gender-fluid icon has given us so many looks on the world’s red carpets that it would be impossible to exclude him from this list. Porter gained attention at the 2019 Golden Globes for wearing an embroidered suit and pink cape designed by Randi Rahm. Just when we thought he could not top himself, he returned to make fashion waves that year with a fitted tuxedo jacket and a velvet gown by Christian Siriano with 6" Rick Owens boots to the 91st Academy Awards. Now that’s an icon.


Honourable mentions:

Arca, Violet Chachki, Adore Delano, Eddie Izzard, Mick Jagger, Lil Nas, Andy Warhol, Amanda Lepore, Andre 3000, Lenny Kravitz, Divine and Lady Gaga.

Kwaai Boutique offers gender-bending loungewear, streetwear and accessories for those who aren’t afraid to break the fashion rules.

Who are your favourite gender-bending icons? Comment below

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