ONE OF THE EARLIEST literary depictions of gender bending can be found in Homer’s Odyssey, telling of the adventures of the mythical hero Odysseus, after the fall of Troy in 1200 B.C., as he makes his voyage home. “Bright eyed Athena,” sometimes also referred to in the transgender community as the “Bigender Goddess,” acts as the protector of Odysseus while he journeys. Athena shape-shifts into different guises, one of which is that of a male warrior, in order to visit Odysseus’s son, Telemachus:
She flashed down from the heights of Olympus, and on reaching Ithaca she took her stand on the threshold of the court in front of Odysseus’s house; and to look like a visitor she assumed the appearance of a family friend, the Taphian chieftain Mentes, bronze spear in hand. … [Telemachus] caught sight of Athene. … He went straight up to his visitor, grasped his right hand, took his bronze spear and gave him cordial greetings. “Welcome, friend!” he said.
Little is known about Homer, and some academic studies even theorize that The Odyssey and The Iliad were written by a woman rather than the man Homer is generally presumed to be. Regardless of the identity of the author, Athena’s act of gender-morphing gives her a powerful and fascinating status as a sacred figure in mythology.
Two millennia later, in medieval France, one of the most extraordinary episodes in theological and political history occurred when the sixteen-year-old Joan of Arc claimed to have been instructed by the Archangel Michael to fight against the English, and boldly went to the Dauphin with the message that she had been sent by God. In full armor, she proceeded to lead an entire division of soldiers to the City of Orléans, where she was hailed a heroine, until a series of misfortunes caused her to be put on trial by the Inquisition. The primary reason for the trial was not heresy but her male attire. Scholar Marjorie Garber writes in her book Vested Interests: “No less than five charges against her detailed her transvestism as emblematic of her presumption: she was unwomanly and immodest, ran the charges, she wore sumptuous clothing to which she was not entitled by rank, and she carried arms.” Even at the trial Joan refused to remove her masculine attire, which had been donned as a direct consequence of her religious “visions.” She declared that she had been commanded by spiritual voices to wear male clothing, and that she would “rather die than relinquish these clothes.” She was convicted and burned at the stake, only to become a French national heroine and eventually a saint.
Women from the 16th century onward are known to have cross-dressed with the intention of “passing” as men so as to follow the careers barred to them. And they occupy the whole class hierarchy, from the highly respected physician and surgeon Dr. James Barry—who served as Inspector General of the British Army’s Medical Department for over forty years until “his” death in 1865, after which Barry’s true gender was discovered—to various pirates. Among the latter class were two women who became famous for their adventures as Ann Bonny and Mary Reed in the 18th century. Bonny had initially fallen in love with Reed, not realizing that behind the masculine facade “he” was also a female. The two subsequently became close comrades and friends.
But the motives for many early cross-dressing women were based on a desire to be liberated from the social constraints imposed upon them. As historian Lillian Faderman commented in Surpassing the Love of Men (1981): “Transvestites were, in a sense, among the first feminists. Mute as they were, without a formulated ideology to express their convictions, they saw the role of women to be dull and limiting. They craved to expand it, and the only way to alter that role in their day was to become a man.” Faderman adds that public cross-dressing could be linked with lesbian identity, though records of these women being physically attracted to other women are rare.
Such was the case for the central character in a 2011 film, Albert Nobbs, set in 19th-century Ireland, and starring Glenn Close as “Albert”: a woman passing as a man in her work as a member of staff at a hotel. The idea of a lesbian relationship doesn’t seem to have occurred to her until she meets another cross-dresser who has “taken a wife” and lives a contentedly married life. Viewers are left wondering about the precise identity of Albert, whose subsequent aspirations to raise the status of her cross-dressing lifestyle by becoming a husband and setting up her own business seem to stem from a keen desire for full equality in society, rather than genuine lesbian attractions. Generally speaking, until the 20th century, passionate attachments between women, including those we now know to have been sexual relationships, were considered by much of society to be intensely affectionate but platonic bonds, particularly idealized in 18th century society as “romantic friendships.”
Nevertheless, this term took on new meaning with the two “ladies of Llangollen,” Sarah Ponsonby and Eleanor Butler. In 1775, the two Irishwomen, determined to lead a life together, eloped and eventually settled in the Welsh town of Llangollen. They cropped and powdered their hair and wore outfits which from the waist up strikingly resembled male attire. Elizabeth Mavor’s compilation of diary entries and accounts includes a letter written by John Lockhart in 1819 after visiting the Ladies, relating that they were “dressed in heavy blue riding habits, enormous shoes, and men’s hats, with their petticoats so tucked up, that at the first glance of them, fussing and tottering about their porch in the agony of expectation, we took them for a couple of hazy or crazy old sailors.” Although reliant on others for financial support after being largely disowned by their families, they existed in an exclusive union of “sweet and delicious retirement” for over fifty years, until Eleanor died in 1829. The Ladies and their home, Plas Newydd, won the admiration of many, including the famously candid lesbian diarist of their time, Anne Lister from Halifax, Yorkshire. Lister was also known for her masculine sense of style and in certain enlightened circles acquired the nickname “Gentleman Jack.”
WITH THE DAWNING of the 20th century, masculine dress among women took on a new significance as it became an overt expression of lesbian identity. It was also closely bound to social status and class, and only those of considerable financial means could afford to cross-dress in the upper-class manner that became the vogue.
England in the 1920s saw the emergence of the painter Gluck and the novelist Radclyffe Hall, both of whom dressed in male clothing full-time while living openly with their lesbian partners. Hall’s famous novel The Well of Loneliness presented lesbianism as a “social problem” in order to introduce the theme into mainstream publishing. At the same time, sexologists such as Havelock Ellis and Richard von Krafft-Ebing were promulgating dubious theories on the psychology of relationships between women, female masculinity, and lesbian, bisexual, and transgender identity. Pseudoscientific terminology such as “invert” now became popular. Hall, aware that “accepting” such labels could give her the power to ultimately transcend them, referred to herself as an invert—and even got Havelock Ellis to write the introduction to the novel.
At first accepted and highly commended by many readers, deliberately scathing reviews by a journalist hoping to stir up scandal caused an infamous court case over The Well of Loneliness, and the book was eventually banned on the grounds of “obscenity.” One of the passages cited highlighted the masculinity of the novel’s wealthy central character Stephen (a woman): “She would go into Malvern that very afternoon and order a new flannel suit at her tailor’s. The suit should be grey with a little white pin stripe, and the jacket, she decided, must have a breast pocket. She would wear a black tie—no, better a grey one to match the new suit with the little white pin stripe.”
Many of the women who wore male attire from the Edwardian era onward were members of artistic and literary circles. They were women of the upper classes who were no longer willing to live secondary lives in disguise. Much of the motivation behind female cross-dressing at this time was to present a provocative and controversial image to the world, defiantly declaring one’s nonconforming identity. The poet Nathalie Barney held “Sapphic” soirées at her Paris salon, which numerous women attended, including many cross-dressers, for lively debate on lesbian and gay society and its contributions to the arts. Over in London, Virginia Woolf, a member of the famous Bloomsbury circle, was writing the novel Orlando, which chronicled the journeys of the title character over a series of centuries. In each century Orlando takes on a different gender and persona, and the precise identity of the hero/heroine becomes indeterminate.
Orlando was actually inspired by one of Woolf’s lovers, the author Vita Sackville-West, who appears cross-dressed in photographic illustrations for the novel and who in real life disguised herself as a man when she eloped with Violet Trefusis in 1919. At this point female transvestism had taken on an aura of glamour and thrill. Sackville-West later described the experience in Portrait of a Marriage with a sense of elation, almost as if she were role-playing in an elaborate game:
I used to stroll about the boulevards as I had strolled down Piccadilly, I used to sit in cafés drinking coffee, and watching people go by; sometimes I saw people I knew, and wondered what they would think if they knew the truth about the slouching boy with the bandaged head and the rather voyou [rogue or hoodlum]appearance, and if they would ever recognize the silent and rather scornful woman they had perhaps met at a dinner-party or a dance? I never appreciated anything so much as living like that with my tongue perpetually in my cheek, and in defiance of every policeman I passed.
Cross-dressing at this point was akin to what we would call today a “fashion statement.” The sensational and usually feminine French author Colette was photographed in drag in 1910, coyly looking at the camera, one hand suggestively poised with a cigarette emitting faint wisps of smoke. In The Pure and the Impure, she speculated about what the Ladies of Llangollen would have been like had they lived in 1930: “They would own a car, wear dungarees, smoke cigarettes, have short hair, and there would be a liquor bar in their apartment. Would Sarah Ponsonby still know how to remain silent? Perhaps, with the aid of crossword puzzles. Eleanor Butler would curse as she jacked up the car, and would have her breasts amputated.” Although controversial at the time, today the image of Sarah Ponsonby doing crossword puzzles while her partner “jacks up” the motor car in dungarees puts the Ladies in yet another quaintly archaic setting.
In the late 19th and early 20th centuries, female cross-dressing in a theatrical sense had found a fresh public appeal, as male impersonators of the London music hall circuit took to the stage. The three most famous women to embark upon such careers were Ella Shields, Vesta Tilley, and Hetty King. They also performed in female roles, although Tilley eventually communicated a decided preference for performing in male persona, commenting: “I felt that I could express myself better if I were dressed as a boy.” Transvestism on stage, as a purely theatrical representation of identity, has always been granted privileges denied to those instances of cross-dressing which merged into reality and presented a perceived danger to the social order. Women who performed as men were generally presumed to restrict their masculinity to the area of entertainment only. It is worth noting that initially the term “drab”—“dressed as a boy” was used for female cross-dressers. The now universal term “drag” was derived from the opposite acronym “dressed as a girl.”
Vesta Tilley, Hetty King, and Ella Shields became highly esteemed in mainstream London theaters. Each had a repertoire of characters, including soldiers, sailors, cowboys, factory workers, and “toffs.” Vesta Tilley’s “Burlington Bertie from Bow” is perhaps the best known of these character routines, comprising lyrics attributed to the songwriter William Hargreaves that make farcical commentary on the serious subject of class divides: “I’m Burlington Bertie, I rise at ten thirty/ And saunter along like a toff. I walk down the Strand with my gloves on my hand/ Then I walk down again with them off. … Nearly everyone knows me from Smith to Lord Rosebr’y, I’m Burlington Bertie from Bow.”
After the success of these early performers, cross-dressing for women on the stage was limited mostly to the role of pantomime prince, Peter Pan, and occasionally Captain Hook. The role of the male impersonator, with a genre and relevance of her own, pretty much vanished from the theatrical program for a considerable time. It is likely that theories being popularized by Havelock Ellis and his ilk had brought new implications to male impersonation in relation to one’s sexual identity, and caused a veil of secrecy to descend upon theatrical platforms for the female transvestite.
However, this figure had also found her way into the movies. As early as 1916, Charlie Chaplin’s leading lady, Edna Purviance, appeared disguised as a male character in Behind the Screen. Even before this, in 1915, the actress Minerva Courtney had successfully impersonated Chaplin in her own version of his comedy The Champion. Chaplin himself was a gifted female impersonator, and at the beginning of his career cross-dressed onscreen a few times. Marlene Dietrich, who once said “I am at heart a gentleman,” appeared wearing top hat and tails in the 1930 film Morocco, and with similar aplomb Greta Garbo strode in a princely 1600’s costume across the sets of Queen Christina in 1933, declaring “I shall die a bachelor!” In actual life, Garbo and Dietrich may have been romantically involved for a time—and both undoubtedly had relations with other women—reinforcing the hypothesis that women’s penchant for cross-dressing is highly correlated with an attraction to other women.
In 1935, the film Sylvia Scarlet was released starring Cary Grant and Katherine Hepburn cross-dressed as a boy. One is struck by how natural Hepburn appears in this masculine persona. Lively and engaging in male attire, she becomes visibly uncomfortable and restricted when she puts on the “appropriate” clothes for her gender. This movie foreshadowed other, similarly plotted films involving female-to-male gender-bending. Among these was the 1982 film Victor Victoria starring Julie Andrews as an unsuccessful female singer who becomes famous disguised as a female impersonator. In the same year, Tootsie was released, this time exploring the theme of male-to-female cross-dressing, with Dustin Hoffman playing an out-of-work actor whose drag persona gains him public acclaim. The following year Yentl came out, starring Barbra Streisand as a Jewish girl who disguises herself as a boy to pursue an education.
IN THE 1960s AND ’70s, the rise of the Second Wave Feminist movement gave women increased freedom of speech and expression, socially, economically, politically, and personally. The fight for women’s liberation became central to countless lives, and lesbian feminism ensured that love between women was viewed not only as an expression of personal commitment but also an extension of political consciousness. In 1977, the poet Elsa Gidlow asserted that “The lesbian personality manifests itself in independence of spirit, in willingness to take responsibility for oneself, not to take ‘authorities’ and their dictum of trust. … The important point is that the lesbian has sought wholeness within herself, not requiring, in the old romantic sense, to be ‘completed’ by an opposite.”
Women of all classes began to cross-dress in an integrated way, wearing “butch” attire, no longer to emulate men, but as a serious and non-theatrical mark of lesbian identity, with masculinity becoming a celebration of womanhood rather than a defiance of it. Clothes originally designated to denote male identity became symbols of women’s strength and liberation. With the rise of transgender equality, those who felt unaligned with their biological gender finally won the right to assert their true identities. Clearly those who have transitioned in this way are no longer cross-dressing but instead enacting the customs of their acquired gender identity.
The 1970s also saw the revival of the male impersonator in America, this time as a “drag king.” Now the illusion was a much more modernist statement than the quaint routines of the music hall: the new era of male impersonation promoted an assertive realism that included “binding” the chest and “packing” the crotch area to create a masculine physique. Crepe wool beards and stubble created facial authenticity. In the 1980s and ’90s, performers such as Annie Lennox and k.d. lang began to introduce female masculinity, drag, and androgyny into mainstream popular culture. The year 1998 saw publication of Sarah Waters’ novel Tipping the Velvet, portraying Victorian male impersonation through a memorable lesbian narrative, later adapted as a popular BBC television series.
With the arrival of the 21st century, female cross-dressing has taken a definitive step toward a new era. UK-based vocalist Gizell Timpani, after admiring acts by drag queens, decided to devise an equivalent of her own, restoring an art form mostly uncelebrated in contemporary contexts, bringing it to modern audiences while retaining a respect for the tradition and heritage of female cross-dressing performance. Altering the pitch effects of her voice, she performs a varied repertoire of masculine songs in her drag persona of Valentino King, has appeared on Britain’s Got Talent, at Pride Festivals, LGBT events, and mainstream venues, and is increasingly admired by audiences across the spectrum as an icon for liberated identity expression. In live performance, Valentino is impressively convincing in male role, while retaining eloquent hints of femininity that keep a sense of theatrical mystique at the heart of “his” image.
As the drag king community grows, Valentino inspires many other women to develop their own drag personas. The implications of a king “scene” finding a niche in modern society and LGBT culture are diverse, and reasons for “dragging up” are personal to the individual. Drag kinging in general is a form of transgender expression. For some, this goes no further than cross-dressing for the purposes of performance or socializing. As a portrayal of masculinity with hidden female qualities, this form of extrovert gender-bending creates a powerful contradiction that still inspires and intrigues. There is a fantasy element connected with the drag king world, involving provocative exploration of gendered ideologies and a transcendental presentation of self that takes female masculinity a step beyond mere dress statement or fashion preference.
So, following this long evolution, the heritage of the “woman in men’s clothing” continues to flourish, constantly finding new branches of expression via art, performance, and social politics, challenging and liberating concepts of gender and identity. It holds importance for LGBT culture in general, while retaining its own enduring significance as an ancient tradition manifesting itself in a modern world.
Clare Wall is a U.K.-based entertainer, writer, and researcher who performs regularly as a male impersonator.