Even if gender-neutral clothing is becoming more in vogue in the main stream and in popular culture, that certainly wasn’t always the case.

As recently as 2012, model Andrej Pejic made headlines when he modelled as both a man and a woman on some of the world’s biggest fashion runways. As ridiculous as you might think it, celebrities that appear on the red carpet in clothing that does not exactly match their gender still set tongues wagging.

Imagine the controversy when celebrities and musicians in the 1930s and even the 1980s stepped into the public eye, sporting looks that were, to say the least, unconventional.

They used to be shunned for appearing in public while dressed this way, but today we see them as trendsetters and fashion icons who were far ahead of their time.

Radclyffe Hall

Considered a pioneer of androgyny, Radclyffe Hall was an out lesbian in the early 20th century (Hall might rather identify as trans today) who often assumed the male pseudonym John, and presented in a very masculine way, wearing smoking jackets, monocles, and bow-ties. Hall wrote several novels, but is known best for The Well of Loneliness, a novel about lesbianism, published in 1928.


Marlene Dietrich

Openly bisexual, Marlene Dietrich appeared on the red carpet and on the big screen in tailored suits. Said Dietrich of her love for male attire: “I am sincere in my preference for my men’s clothes – I do not wear them to be sensational. I think I am much more alluring in these clothes.”


David Bowie

Often referred to as the father of androgyny in the 1970s, David Bowie didn’t just pave the way for music – he also did so for fashion. Bowie assumed a number of different personas throughout his career, and his androgynous style is said to have influenced Vivienne Westwood, Jean Paul Gaultier and a number of other designers.



When Prince passed away in 2016, the world mourned a creative icon that never stopped pushing the boundaries. In his 1984 hit “I Would Die 4 U” Prince himself says it best: “I’m not a woman, I’m not a man/ I am something that you’ll never understand”.


Annie Lennox

Annie Lennox’s androgyny was much more than just dressing up. Her choice of clothing was a political and gender statement that seems right at home in 2018. Speaking about her 1984 Grammys Elvis homage, Lennox said: “Women have been wearing men’s clothes for centuries. It’s a powerful thing when a woman wears something less feminine. It’s saying; you must look at me slightly differently, I’m not just going to be a sexual object for you.”


Grace Jones

This Jamaican singer, supermodel and fashion icon embraces androgyny unabashedly. In her autobiography, I’ll Never Write My Memoirs, Jones says: “I never ask for anything in a relationship, because I have this sugar daddy I have created for myself: me. I am my own sugar daddy. I have a very strong male side, which I developed to protect my female side. If I want a diamond necklace I can go and buy myself a diamond necklace.”