Marlene Dietrich: suits you, sir
2. Elvis Presley
Elvis Presley rose to fame in the 1950s with his distinct rock & roll sound and his unique sense of style. He was one of the first male stars to openly use make-up, and this later inspired other performers, such as The Beatles, Mick Jagger and Jimi Hendrix, to experiment with androgyny.
Elvis inspired the androgynous Rockabilly trend in the USA, which saw girls defy gender norms by dressing in tomboy clothing and wearing their hair in masculine-style quiffs.
Elvis Presley: Shook us all up with his Rockabilly rags
3. The Beatles
Entering the music scene in the early 1960s, English rock band The Beatles inspired a whole new era of androgynous style.
They changed the 1950s male image of slicked back quiffs and leather jackets with their controversial long hair and high-heeled boots, and despite some initial outrage at their open disregard of gender rules, they inspired a generation of men to experiment with androgynous dressing.
The Beatles' longer hairstyles inspired millions of boys
Harris Glenn Milstead rose to fame in the early 1970s, performing in theatre and in film dressed as his drag queen persona Divine. One of the first and most famous drag queens, Divine developed a reputation for his trashy, crude and often obscene behaviour.
He gained a large following of supporters and was particularly well received in the gay community. Although he passed away in 1988, he remains a popular cult figure and was named by People
magazine as ‘Drag Queen of the Century’.
Divine: big, beautiful and bold as hell!
5. David Bowie
The glam rock era of the 1970s saw the lines for gender conformity blurred even further, with male artists such as David Bowie proudly performing in tight, feminine clothing and wearing make-up.
Bowie's androgynous long haired alter-ego Ziggy Stardust was hugely popular, showing just how much society had changed its view on what was acceptable.
David Bowie: a true gender-bending icon
6. Dr Frank N. Furter
When it was released in 1975, The Rocky Horror Picture Show
was mostly ignored by audiences, and described as tasteless and pointless by critics.
The film follows the story of a young heterosexual couple who stumble across the castle of Dr Frank N. Furter when their car gets a flat tyre.
The film is a celebration of trans dressing
and very much embraces and encourages breaking the boundaries of gender conformity.
While the movie was initially not very well received, it soon began to gather a growing number of straight, gay and trans fans, who would attend showings at the cinema dressed in drag, and today has a large international following of devotees who regard it as one of the best cult films ever.
Rocky Horror: surely the best drag film of all time?
The late 1970s and 1980s saw the boundaries of gender conformity well and truly smashed, with a number of pop and rock icons who ignored all the rules and made gender bending something to be embraced and flaunted.
One such artist was Prince, who wore flamboyant girlish outfits of frilly shirts, skin-tight trousers, platform heels and heavy eye make-up. Prince was, and still is, adored by men and woman alike, and is widely considered to be one of the greatest musicians of all time.
Who didn't have a crush on Prince?
8. Annie Lennox
While it had become quite acceptable for men to work the androgynous angle, when Annie Lennox came onto the music scene in the late 1970s gender bending still wasn’t something pop culture had seen women do much of.
Dressing in men's suits and with her short, masculine haircut, Lennox stood out for all the right reasons. She shocked and delighted audiences when she performed as a drag king at the Grammy Awards in February 1984, showing that gender bending was not just a man's game.
Lennox's image is widely imitated today, with it now being considered fashionable and sexy for women to dress in male clothing, and her unique and unforgettable style is often seen replicated by female stars on the red carpet.
With her short, cropped hair and masculine suits, Annie Lennox made dressing as a man cool
9. Boy George
The glam rockers of the '70s really paved the way for the New Romantic wave of music, which was heavily influenced by the androgynous image of its predecessors.
With it came a new trend of extreme gender bending, to the point where it was argued that some artists of the era were trans dressing.
Boy George was one performer who fully embraced this image, with his iconic heavily made-up face consisting of colourful eyeshadows, heavy eyeliner, blusher and lipstick.
With his long hair and feminine outfits, he could almost be mistaken for the opposite sex, but by this point culture accepted and welcomed his glamourous appearance.
With his love of lipstick and make-up, many thought Boy George was a girl when he broke onto the scene
By the time RuPaul became famous in the 1990s, pop culture had very much been exposed to extreme gender bending, drag and trans performers and he was accepted and embraced by the public, who loved his work.
Today, RuPaul is still a popular musician, actor and television personality, and appears in public and performs both in and out of drag, proving just how far society has come over the last century.
RuPaul: supermodel of the world and fierce, gender bending icon