The Original Flamboyants

A celebration of men throughout history who have pushed the boundaries of fashion.

Inspired by our interview with designer Harris Reed this week, here we highlight others who bravely chose freedom from the confines and expectations of traditional gender norms, characters whose sexuality refused to be defined by their clothing.

We have lived in a patriarchal social system for centuries, where women had to cross-dress to pass as men in order to live a bolder life and access any kind of economic independence. On stage, women were prohibited from performing, so men and young boys would often step in to female roles. Then female impersonation started to become commonplace, but this was usually played with comedic intent. Only after censorship loosened in the 1950s, did cross-dressing roles started to appear in serious dramas.

Women dressing as men has historically been met with a more favorable attitude than vice versa. It depicted a gender driven forward movement in terms of social status, power, and freedom. However, when men cross-dressed as women, they were generally looked down upon because they therefore automatically lost status.

The following selection of enthusiastically outrageous dressers continue a centuries old tradition of flamboyance which fortunately endures to this day, and more and more without condemnation. From the dandies in the 19th century, through the emergence of drag culture in the 1930s, the sexual revolution of the sixties and glam rock in the 1970s, to punk and the new romantics in the 1980s … are we finally reaching a time of gender blurring acceptance, and wearing whatever we want without judgement?

To quote Iggy Pop: “I’m not ashamed to dress ‘like a woman’ because I don’t think it’s shameful to be a woman.”

Oscar Wilde (16 October 1854 — 30 November 1900)

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Oscar Fingal O’Flahertie Wills Wilde, the Anglo/Irish poet, playwright, essayist and journalist, was recognized for his dandy dressing style as well as his timeless prose. An exceptional classicist, he became associated with the emerging philosophy of aestheticism. Famous for his biting wit, flamboyant dress and glittering conversational skill, he was convicted in one of the first ‘celebrity’ trials for gross indecency for consensual homosexual acts and served two years hard labor in prison before dying in Paris from Meningitis aged 46. Wilde was posthumously pardoned for his conviction along with 50,000 other men under the UK’s ‘Turing Law’ in 2017.

Henry Paget, 5th Marquess of Anglesey (16 June 1875 — 14 March 1905)


Born into aristocratic privilege, Henry Cyril Paget, otherwise known as ‘Toppy’, swiftly acquired a reputation for his lavish and spendthrift manner of living. He used his inheritance to buy jewelry and furs, to host extravagant parties and play the starring roles in elaborate theatrical performances. He was dubbed ’the dancing marquess’ referring to his version of ‘Butterfly Dancing’, where a voluminous robe of transparent white silk would be waved like wings. His was a short and hedonistic life, passing from tuberculosis at aged 29, in massive debt, his creditors taking possession of his beloved Charvet dressing gowns and custom made jewels as way of settlement.

Little Richard (December 5, 1932 — May 9, 2020)

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Nicknamed ‘The Innovator’, ‘The Originator’, and ‘The Architect of Rock and Roll’, Richard Wayne Penniman is cited as one of the first crossover black artists, reaching audiences of all races. His music and concerts broke the color line, drawing black and white people together despite repeated attempts to sustain segregation. Elvis Presley famously told Richard in 1969 that his music was an inspiration to him and that he was “the greatest.” Non-conformist and unapologetic in his dress, he helped usher in an era of bombastic menswear, inadvertently becoming a style pioneer and inspiration for those fearless enough to follow.

Shi Pei Pu (December 21, 1938 — June 30, 2009)


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Shi Pei Pu was a Chinese dramatic actor and opera singer from Beijing. He became a spy who obtained secrets from an employee in the French embassy, called Bernard Boursicot, during a 20-year-long sexual affair in which the performer convinced Boursicot that he was a woman dressed as a man, due to the fact that his father had wanted a son. Their affair was maintained in darkness and Shi also claimed to have had a child that he insisted had been born through their relations. Following both men being convicted and jailed for espionage, the scandalous story made headlines in France and his eccentric character inspired David Henry Hwang’s play ‘M. Butterly’ (1988) which was produced on Broadway and adapted as a movie in 1993. In April 1987, as part of an effort to defuse tensions between France and China over what was described as a “very silly” and unimportant case, both men were pardoned.

David Bowie (8 January 1947 — 10 January 2016)


Singer, songwriter, actor and musician David Robert Jones was one of the first of his generation of stars to publicly experiment with the power of androgynous fashion. Whether on stage as one of his self-possessed characters or in his personal life, he was never perturbed by other’s judgement and completely committed and aware of the provocative value of an intoxicating costume. Two of his most famous incarnations, ‘ The Thin White Duke’ and ‘Ziggy Stardust’ garnered, and still maintain, a deity like status in popular culture.

Grayson Perry (born March 24th 1960)


The British Turner Prize winning artist is more frequently recognized when dressed as his alter ego, Claire, and also includes her regularly in his work. Perry has been cross-dressing since he was in his teens, and designs the outfits himself. He also presented two documentaries, ‘Why Men Wear Frocks’, in which he talks about his own life as a cross-dresser, and how it affects his wife and child; and ‘Grayson Perry: All Man’, discussing masculinity in today’s world.

Leigh Bowery (March 26th 1961 — December 31st 1996)

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A darling of the fashion world who left behind a hugely influential legacy, Leigh Bowery was an Australian performance artist, club promoter (he created Taboo in London) and designer, renowned and frequently imitated for his wildly extreme make up and elaborate costumes. Bowery was also a muse and model for painter and friend Lucian Freud, who described the private man as shy and gentle, and his outrageous persona as a form of self-defense.

Dennis Rodman (born May 13, 1961)

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Nicknamed ‘the Worm’, Dennis Keith Rodman is an American former professional basketball player almost as memorable for his piercings, make up, and headline grabbing attire as he is for his fierce defensive and rebounding abilities. Famously wearing a wedding dress to promote his 1996 autobiography ‘ Bad As I Wanna Be’ one cannot underestimate his talent in understanding and embracing the exhibitionist advantages of cross-dressing, especially so within the predominantly ‘masculine’ boundaries of professional sports.

Prince (June 7th 1958 – April 21st 2016)


This legendary singer, songwriter, and multi-instrumentalist was also the modern dandy of rock, funk and pop. His signature style, incorporating pussy-bow blouses teamed with lame suits, high heel, lingerie, lace and a love of make up, was a precursor to today’s trans-aware moment. This ambiguous style was key in making him a sex symbol for a generation, and also possibly the only rock star to have a Pantone color named in his honor, a shade of purple naturally.

Eddie Izzard (born February 7th 1962)

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Eddie Izzard has the in the past described herself as “a straight transvestite,” “a male lesbian,” and “a complete boy plus half girl.” The comedian also admits that trying to define her sexuality is confusing, but that has never stopped her fully expressing herself through her wardrobe, and advocating for non-conformative dressing… “They’re not women’s clothes. They’re my clothes. I bought them.”

Billy Porter (born September 21st 1969)

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Billy Porter openly admitted that wearing a dress to the Oscars in 2019 was a ruse to get noticed, because getting noticed gets him work. The ‘Pose’ actor felt frustrated that women had more fashion options than men, and wanted to challenge the patriarchy of ‘penguin suits’ for men. Porter claims his life turned around as soon as he stopped worrying about societal norms, and since then his influence on red carpet style has only grown in positivity, leading to him ultimately being labeled by Time magazine as a fashion icon.

Ezra Miller (born September 30th 1992)


The striking and talented 28 year old ‘Fantastic Beasts’ actor is known for their sartorial courage, challenging the norms of movie premiere appearances with gender free looks by high end designers such as Pierpaolo Piccioli for Moncler, Givenchy and Burberry. Vocally dismissive of the need to gender identify, Miller told The Hollywood Reporter “I don’t identify as a man, I don’t identify as a woman. I barely identify as a human.”

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