In March of 2022, Florida passed the Parental Rights in Education Bill – referred to by critics as the ‘Don’t Say Gay’ Bill – which bans discussion of sexuality and gender identity within classrooms of children under the age of nine. The exposure of such young children to overtly sexual concerns, proponents claim, should not be the aims of schools; educational institutions should provide “an education, not an indoctrination”. This sentiment has been continued by various bans on drag shows across the US. Yet, given the prevalence of cross-dressing within education and society far beyond, featuring prominently not only in Shakespearean literature, but even in Greek, Norse, and Hindu mythology (perhaps most well-known is Thor’s transformation into his wife, Freyja, in order to retrieve his stolen hammer), this striking opposition is somewhat surprising. 

In his book Gender in Play on the Shakespearean Stage, Michael Shapiro lists eighty plays that feature cross-dressing during Elizabethan England. One-fifth of the plays of Shakespeare – who was, perhaps, largely inspired by Queen Elizabeth I herself – fall into this category. Indeed, her reign, spanning almost half a century, urged on the humanist-led movement for the general betterment of women within society; remembered simultaneously for being the ‘virgin queen’, establishing Protestantism in England, and defeating the Spanish Armada in 1588, Elizabeth challenged previously patriarchal-owned terms of authority, intellectuality, and even masculinity. Shakespeare reflects on his powerful contemporary influences by utilising female-to-male transformations in his plays as part of the ‘social progress’ narrative. For example, in Shakespearean convention, by cross-dressing, women are able to ascend both to higher social positions and to typically masculine virtues (heroism and courage). In fact, three of Shakespeare’s comedies show patterns in his attitudes and depictions of such a physical, emotional, and psychological change in three different women: The Merchant of Venice (1596), Twelfth Night (1600), and As You Like It (1600).

For instance, three characters (Portia, Viola, and Rosalind) adopt a male façade in order to further their goals throughout the play; their first step is often to disguise their appearance. Here, the physical preconceptions of masculinity and femininity are seen in the changes made to each woman. Before protecting her lover’s interests in court, Portia (The Merchant of Venice), for example, promises to “turn two mincing steps into a manly stride”, and “speak between the change of man and boy, with a reed voice”. It is also specified that she enters “dressed like a doctor of laws”, rendering the court’s perception of Portia’s gender plausible – a woman wearing men’s clothing would have been sexually immoral to an unthinkable degree, so it follows that the lawyer must be male. Additionally, Rosalind (As You Like It) has the benefit of being more than “common tall”, but goes to the effort of arming herself with “a gallant curtle-axe” and a “boar-spear” as she journeys to the Forest of Ardenne; such a long journey would not be safe for two women (Rosalind and her cousin, Celia) by themselves, and so Rosalind becomes Ganymede – a Trojan prince who, in Elizabethan England, was used as a metonym for young men who engaged in traditional same-sex dating practices, adding further to the multi-faceted notion of gender in As You Like It. Shakespeare’s characterisation of women becoming men partially relies on these characters adopting preconceptions of male physicality; only thus can their lack of passivity be justified.

Shakespeare’s women also portray what was perceived to be the innate male determination and backbone, and use cross-dressing as a means to achieve their desired love which was otherwise unattainable. As women, these three characters are restricted by various branches of the patriarchy – Viola is unable to serve Countess Olivia, whilst Rosalind is exiled purely out of association to her father, and Portia is unable to choose whom she marries. However, although they do not gain any more humanity as a result of becoming men, their existing emotional maturity is more readily accepted by the other characters (and presumably the contemporary audience). For example, Rosalind’s tutorship of Orlando would likely be unwelcome at the time, so she disguises herself as a young man to guide her student to becoming a more thoughtful lover, ultimately to her own benefit. Yet, Rosalind dominates As You Like It, and her characterisation goes deeper than any other in the play – it seems evident that she has settled for someone incomparable to her subtlety of thought. For instance, in response to Orlando blaming his tardiness on the lack of clocks in the forest, she quips “then there is no true lover in the forest, else sighing every minute and groaning every hour would detect the lazy foot of time as well as a clock.” Still, upon reverting back to her female form, when she wholeheartedly declares her love for Orlando, she not only submits to his will but also sheds the necessity to appear intellectually and psychologically superior to him. Shakespeare’s depiction of the gender dichotomy is unrelentingly entrenched in his contemporary worldview – after all, women are only able to access higher echelons of ‘thought’ by presenting themselves as men.

Perhaps on account of the limitations of actors at the time (female roles were played by young boys, for example), Shakespeare does instil a certain degree of androgyny in these characters. And, by doing so, he reinforces the theme of illusion and perception that is key to so many of his comedies. Although Portia’s remarkable status, adventurousness, and shrewd cunning defines her character both male and female, she remains obedient to her dead father’s wishes regarding her spouse: contemporary attitudes to servitude would naturally associate this with femininity (arguably, still today). Furthermore, while her suggestions of sexual promiscuity (“I’ll not deny him of anything I have”) are laced with masculinity – men contemporarily seen as being the ‘agents’ of sex, they are contrasted by her actual fidelity to her husband, and the handing over of her fortune and rule over her city to him. However, while Portia is striking in her ability to display such dazzling heights of masculinity – intellectuality — Viola appears to be the most feminine of the three. At times, Viola even considers her manipulation of gender to be a deformity, stating “[d]isguise, I see thou art a wickedness”. Initially, Viola sees her disguise as an opportunity to ensure her safety, but she comes to realise throughout the play that it also creates issues for her – namely, another woman falling in love with her. Her façade is inherently less ‘masculine’ than that of the other two: whilst Portia becomes a lawyer, wise and rational, and Rosalind becomes a shepherd-cum-love guru, practical and perceptive, on the contrary, Viola becomes a eunuch. Additionally, Viola’s gender is contrasted to her brother, Sebastian, throughout the play, and the siblings together are often associated with androgyny themselves. When the two are reunited, therefore, it is necessary that they balance each other out, so Viola’s reverts to its female form. Ultimately, these three characters are essential to the plots of their respective stories for their transformation of gender. However, the women’s changed appearances and newfound resourcefulness, contrasted to their supposed frailty and subservience, presumably only added to the comedic nature of these characters and plays. 

By donning men’s clothes and adopting their man-nerisms (!), Shakespeare’s women transgress the gender boundary and are rewarded with the privileges of the ‘more advanced’ sex. Released from the private sphere of the domestic world, Portia, Viola, and Rosalind are able to travel safely and enter public society. As a result of these societal benefits, too, characters around these women (as well as Shakespearean audiences) embrace and respect their virtues – intelligence, courage, wisdom – albeit as men. Still, it is important to recognise that Shakespeare’s portrayal of gender serves to break down the dichotomy of gender presentation and identity: by displaying a degree of androgyny in these women, the combination of masculine and feminine qualities are seen to exist together, reinforcing the idea that these are not two polar opposites. The combination of ‘male’ and ‘female’ physical and emotional worlds shows that, within his characters, Shakespeare is able to instil more profound conflicting impulses than merely ‘male’ and ‘female’. After all, dichotomies of freedom and oppression, reality and deception, and beauty and imperfection are far more interesting than any anachronistic presentations of gender.