Challenging Gender – in Pictures

Gender has been a popular topic in the art world recently, with many contemporary artists challenging the the socially constructed binary between feminine and masculine.

This isn’t something totally new however. We had a look in the archives for people and artists that have challenged the gender binary in the last 100 years, in doing so paving the way for contemporary artists today. This collection of images is separated into three different art forms: painting, photography, and drag.


These beautiful paintings all explore themes of gender fluidity, self-expression and androgeny. In Frida Kahlo‘s self-portrait, she keeps her signature thick eyebrows and slight moustache, but swaps her usual long hair and full length dress for a short crop and dark blue suit. The colours and themes match beautifully with Paula Rego‘s more contemporary Vanitas.

Left: Vanitas, 2006 (triptych) (pastel on paper on board), Rego, Paula (b.1935) / Private Collection / Bridgeman Images
Right: Self Portrait with Cropped Hair, 1940 (oil on canvas), Kahlo, Frida (1907-54) / Museum of Modern Art, New York, USA / Photo © Fine Art Images / Bridgeman Images
Left:  Pasha with red book, 1909 (oil on canvas), Konchalovsky, Petr Petrovic (1876-1955) / Private Collection / Sputnik / Bridgeman Images
Right: Total Androgyny; Totalite Androgyne VI, 1961 (oil on canvas), Brauner, Victor (1903-66) / Private Collection / Photo © Christie’s Images / Bridgeman Images
Left: La Garconne, 1928 (oil on canvas), Kisling, Moise (1891-1953) / Private Collection / Photo © Christie’s Images / Bridgeman Images
Right: Les Travestis, 1927 (oil on canvas), Janin, Jean (1898-1970) / Private Collection / Photo © Christie’s Images / Bridgeman Images


Black and white photos can feel old or outdated, but a rawer, less filtered vintage touch is something much desired in art today. The content of these photos are in many ways still radical today in spite of their age.

This is demonstrated best by French writer Colette, who defied gender stereotypes at the start of the 20th century by writing about powerful female characters and wearing men’s clothes. The 2018 film Colette tells the story of her life over 60 years after her death, in a time where her actions are still seen as pushing the boundaries of the gender binary.

Left:  Portrait of Leif and Paal Roschberg, The Rocky Twins , c.1926 (photo) / Private Collection / Prismatic Pictures / Bridgeman Images
Right:  French writer Colette (1873-1954) wearing man ‘s suit and smoking, photographed by Henri Manuel, c. 1909 / PVDE / Bridgeman Images
Left: Cross Dressed Man Receiving Message and Flowers / Everett Collection / Bridgeman Images
Right: Self portrait, 1928 (b/w photo), Cahun, Claude (1894-1954) / Jersey Heritage Trust, UK / Bridgeman Images
Left: Portrait of Woman in Suit and Hat / Everett Collection / Bridgeman Images
Right: David Bowie, Wembley, 1978 (b/w photo) / © Mirrorpix / Bridgeman Images


Andy Warhol famously focused on drag in his Ladies and Gentlemen (1975) series and his Self-Portrait In Drag (1982) polaroid photos. However, drag can also be considered an art form in its own right, with carefully thought out performances and wildly creative hair and make-up.

With intimate portraits and hues of pink and red, these images show drag’s focus self-expression and exaggerated femininity.

  Left: Self Portrait in Drag (photo), Warhol, Andy (1928-87) / Hamburger Kunsthalle, Hamburg, Germany / Bridgeman Images
Right: Untitled (Drag Queen), 1977 (synthetic polymer and silkscreen inks on canvas), Warhol, Andy (1928-87) / Private Collection / Photo © Christie’s Images / Bridgeman Images
Left: LA CAGE AUX FOLLES, Ugo Tognozzi, Michel Serrault, 1978 © United Artists / Everett Collection / Bridgeman Images
Right: The Dying Swan: Les Ballets Trockadero de Monte Carlo / Bridgeman Images
Left: Close-up of a man in drag Putting Decoration onto Hip and Holding Furry Handbag / PYMCA/UIG / Bridgeman Images
Right: Shhh…, 1990/2012 (digital chromogenic print), Reynolds, Hunter (b.1959) / Addison Gallery of American Art, Phillips Academy, Andover, MA, USA / Bridgeman Images

If you enjoyed these images and want to see more, have a look at our selection of gender non-conformist images.

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