The role of the cross-dressing male in literature for children serves to either reinforce societal gender norms or criticise them. In order for the genre of cross-dressing to exist, however, the implied reader must already live in a society where dress plays a significant part in gender recognition and is generally practised as a social norm. Transsexual activist Nancy Nangeroni quoted that ‘It is not gender which causes problems; rather it is the imposition of gender on an individual by another.’ Due to the socialisation of gender in Western societies, the cross-dressing male in literature for children is treated as the ‘other’. By discussing David Walliams’s novel The Boy in the Dress in comparison to Terence Blacker’s Boy2Girl, Kenneth Grahame’s The Wind in the Willows, and Mark Twain’s The Adventures of Huckleberry Finn, I will identify the key issues surrounding the cross-dressing male in literature for children such as masculine reinforcement, sexuality, humour, and gender performance.
Written in 2008, Walliams offers an original critique of the male child cross-dresser in his novel The Boy in the Dress by addressing the way that clothing can create ‘otherness’. The opening statement of the novel is ambiguous, ‘Dennis was different.’ This statement not only poses the question of what or who is Dennis different from but also puts Dennis into the category of ‘other’. The narrator proceeds by telling the reader that ‘When [Dennis] looked in the mirror he saw an ordinary twelve-year-old boy,’ (The Boy in the Dress, p.11). This implies that Dennis is not ‘different’ because of his appearance but rather because ‘he felt different- his thoughts were full of colour and poetry, though his life could be very boring’ (The Boy in the Dress, p.11). In this quotation, the italicised ‘felt’ in addition to his thoughts of colour and poetry not only demonstrate Dennis’s aesthetic view of the world but also an unconventional representation of the traditional masculine expression. Social theorist Victor J. Seidler suggests that ‘expressing emotions allows men to connect to an aspect of their subjectivity that traditional forms of masculinity have denied them.’  Walliams is demonstrating that Dennis is aware that he deviates from the stereotypical Westernised idea of masculinity and therefore, feels different.
Masculinity in The Boy in the Dress, suppresses the protagonist’s subjective self. Walliams demonstrates this by exploring masculine reinforcement within the child’s family. When Dennis’s mother leaves home, his father makes a rule of ‘No crying. And worst of all- no hugging, (The Boy in the Dress, p.16). For Dennis, his father’s lack of emotion is a result of depression, (The boy in the Dress, p15). Fischer suggests that
men hardly disclose their personal feelings, and tend to conceal the expression of emotions like fear, sadness, shame, and guilt. This can be understood as a strategy to boost conventional masculinity.
By repressing his feelings, Dennis’s father reinforces his masculinity to the detriment of his sons. The repercussions of his behaviour are installed in Dennis’s brother who tells that protagonist that, ‘Only girls cry,’ (The Boy in the Dress, p.17). Walliams demonstrates the effects that masculine reinforcement has on Dennis’s freedom of choice. When the protagonist is encouraged to try on Lisa’s dress, ‘he imagines for a moment what he would look like wearing it, but then told himself to stop being silly, (The Boy in the Dress, p.83). Identifying his discomfort, Lisa reassures him by saying she ‘love[s] putting on pretty dresses. I bet some boys would like it too. It’s no big deal,’ (The Boy in the Dress, p.83). This contemporary reaction to cross-dressing is a result of the ‘differences [that] have been found in the perceptions of men and women towards transgender behaviours and people. In general, women are more tolerant.’  Dennis however, is torn between what he desires and how he has been taught to behave, ‘Dennis’s heart was beating really fast- he wanted to say “yes” but he couldn’t,’ (The Boy in the Dress, p.83-84). Walliams criticises the Western construction of masculinity by showing Dennis’s oppression due to the masculine reinforcement he receives at home.
Unlike Walliams’s criticism of masculinity, Kenneth Grahame’s The Wind in the Willows, published in 1908 promotes masculinity in order to reinforce Western gender norms. The character of Toad is represented as a carefree independent and wealthy animal with a disregard for societal rules. Following his imprisonment for joyriding, Toad’s female prison guard suggests that he dresses as a washerwoman to escape, explaining that ‘You’re very alike in many respects – particularly about the figure,’  The character’s genderless shape allows him the ability to disguise himself. Dress for Toad is one of the ways that he can outwardly expose his masculinity in addition to gender performance and reputation. It is for this reason that he is delighted when the original washerwoman suggests she should be tied and up and gagged before he escapes as she wants to keep her employment, ‘It would enable him to leave the prison in some style, and his reputation for being a desperate and dangerous fellow untarnished, (The Wind in the Willows, p.80). The word desperate in conjunction with dangerous reasserts Toads masculinity as he is proving not only that his cross-dressing is a necessary deviance but one that enhances his power. Moreover, whilst the cross-dressing incident is presented as humorous, ‘Toad’s behaviour simply reinforces the normative gender binary rather than engaging with the subversive function of the carnivalesque.’ For Toad, cross-dressing is a way for him to misbehave and divert attention from his true masculine self and as a result, gender binary is reinforced.
Gender performance is a key trope in male cross-dressing literature and highlights preconceived assumptions of gender roles. In Mark Twain’s Adventures of Huckleberry Finn, published in the United Kingdom in 1884, the protagonist is encouraged to wear women’s clothing in order to obtain information. Huckleberry’s friend Jim suggests that Huckleberry ‘put on some of them old things and dress up like a girl?’ In this instance, the act of cross-dressing is a fun experience and supplemented by an illustration by E. W. Kemble. This shows Jim kneeling down behind Huckleberry and laughing, whilst Huckleberry looks over his shoulder grinning and posing in a feminine manner. Flannigan suggests that
male cross-dressing is used for comedic purposes. The male cross-dresser, adored in feminine apparel worn in such an inexpert manner that his true sex remains no secret is a well-established comedic strategy,’ (Flannigan, p.135).
Flannigan’s suggestion demonstrates the reaction that the cross-dressing male has on its audience but fails to address the problematic response. In order for the act of cross-dressing to be deemed as comedic, the implied reader must already assume that the male character is acting incorrectly according to his perceived gender role. Walliams identifies this problem in The Boy in the Dress, by raising the issue of female inequality and the difficulty of femininity. Lisa suggests to Dennis that it’s ‘Not easy being a girl is it?’ (The Boy in the Dress, p.124). Furthermore, cross-dressing Dennis discovers the difficulty of being a girl:
Remember to cross your legs when you are wearing a dress, and most importantly, Don’t catch the boys’ eyes as you may be more attractive than you thought! (The Boy in the Dress, p.138).
In the above quotation, Walliams explores some of the rules of femininity. Not only is he discussing the female etiquette of ‘cross[ing] your legs’ but also the ways in which girls are sexualised by boys. The exclamation at the close of the quote illustrates male dominance, as it is the female who must divert her eyes from the male. Moreover, when Dennis’s father asks his son if he enjoys wearing a dress, Dennis replies, ‘Well, yes, Dad. It’s just…fun,’ (The Boy in the Dress, p.167). The pause before ‘fun’ suggests that the protagonist is searching for the correct word that will console his father. Walliams is, however, criticising the way in which cross-dressing in literature for children is perceived as humorous. For Dennis, cross-dressing allows him the happiness that he normally suppresses whilst in his conventional male role, ‘He felt so happy he wanted to dance,’ (The Boy in the Dress, p.100). This then raises the question ‘why are girls allowed to wear dresses and boys aren’t? It doesn’t make sense,’ (The Boy in the Dress, p.175). Dennis can see how illogical the typical Westernised view of cross-dressing is.
Sexual orientation is often explored in literature for children when a cross-dressing male is a main character. In Terence Blacker’s Boy2Girl, written in 2004, Sam Lopez, is persuaded to cross-dress as part of an initiation into the Shed gang. The gang decide that Sam should go to his new school wearing girl’s clothes for five days. The novel is written with first person multiple narrators with the exclusion of the protagonist. This immediately demonstrates Sam’s lack of individuality. His first reaction demonstrates a common reaction to male cross-dressing, “You want me to be some kind of fruit?” Fruit or fruitcake is a common slang word that refers to a homosexual.  This association derives from the Victorian fin de siècle when ‘widespread contemporary fear[s] that perversion and deviation [from gender norms were] agents of degeneration.’
This notion is also identified by Walliams in The Boy in the Dress when Dennis is caught by his Head Teacher wearing the orange sequined dress in school. The Head Master expels the boy and tells him ‘I am not having a degenerate like you in my school’, (The Boy in the Dress, p.163). Cross-dressing is often thought of as sexually motivated. ‘Male cross-dressing is perceived as inherently sexual in nature (either in a fetishistic sense or in a homosexual context),’ (Flannigan, p.49). Sam’s reaction to cross-dressing in Boy2Girl demonstrates that the remnants of Victorian fear still remain. Similarly, in The Boy in the Dress, Dennis’s brother suggests that boys who read girls magazines are ‘Woofters!’(The Boy in the Dress, p.56), which is another popular term to describe the homosexual man. Whilst cross-dressing is identified as deviant behaviour in Walliams’s novel, Harrison suggests that cross-dressing can be referred to as:
“Gender Deviance” [which] simply refers to an individual who falls outside of our ordinary everyday understanding of male/masculine and female/feminine.’
This critique raises the question of how the male child cross-dresser can be legitimately deemed as deviant when he is still in the early learning stages of his life and may not be fully aware of the Western gender ideology.
Walliams addresses gender ideology in childhood as problematic. In The Boy in the Dress, Dennis becomes bored due to his confinement within a socially constructed gender role. The word boring is mentioned eleven times throughout the novel and cross-dressing allows him to ‘feel like he [doesn’t] have to be boring Dennis living his boring life anymore’ (The Boy in the Dress, p.107). This quotation illustrates the stifling effect that conformity has over the protagonist. Cross-dressing gives him a feeling of liberty. Walliams demonstrates this freedom through a change in narrative voice, from the third person to first, ‘I can be whoever I want to be,’ (The Boy in the Dress, p.107). The ‘I’, allows the character independent thought, whilst the repetition of ‘be’ gives him freedom of choice and finally ‘whoever’ is gender neutral. The action of cross-dressing gives Dennis insight into life without gender conformity and he tells ‘Lisa I want to thank you for opening my eyes’, (The Boy in the Dress, p.207). Walliams is teaching the reader that gender should not be defined by what one wears.
The idea of gender neutrality is found in Adventures of Huckleberry Finn, the author demonstrates Huckleberry’s non-conformity due to his preference of wearing no clothes and his inability to accept and conform to civilisation:
We was always naked, day and night,[…] the new clothes Buck’s folks made for me was too good to be comfortable, and besides I didn’t go much on clothes, nohow, (Adventures of Huckleberry Finn, Para.3 of Chapter 19).
In the above quotation, Twain demonstrates Huckleberry’s relaxed nature and how he is comfortable in himself without the stifling effects of clothing. In addition, the author points out that adults are a child’s source of clothing, therefore limiting their independence. Huckleberry’s nakedness makes him gender neutral as opposed to conforming to socially constructed masculinity.
Cross-dressing in literature for children is often used to either reinforce societal gender norms or criticise them. Walliams, however, demonstrates that cross-dressing simply means a person who does not conform to Western dress codes. Dennis identifies this in his Sikh friend because he is ‘the only one who [wears] a patka,’ (The Boy in the Dress, p.63). Dennis asks, ‘Do you feel different Darvesh?’(The boy in the Dress, p.63). The emphasis on the italicised ‘you’ alters the tone of the question suggesting that Dennis is aware of segregation due social conformity of dress. Darvesh’s reply allows Walliams to highlight how otherness is socially constructed; ‘When mum took me to India at Christmas to visit Grandma I didn’t at all. All the Sikh boys are wearing them,’ (The Boy in the Dress, p.63). Walliams is demonstrating how alienating clothing can be for children, not only in gender but also within a cultural context.
Walliams, at the end of The Boy in the Dress, addresses exclusion or ‘othering’ due to societal control over children’s dress. In order to include Dennis in the football match after his exclusion from school, the full football team dress in women’s clothing. Suddenly ‘There was a huge cheer from the crowd’, (The Boy in the Dress, p.192). Walliams normalises the act of cross-dressing to demonstrate that exclusion due to gender or cultural dress is unnecessary. The final message in the novel serves to convince the reader that clothes are irrelevant to gender; Dennis notices a red jacket coming towards him ‘And then the red jacket turned into a man,’(The Boy in the Dress, p.196).This defies the contemporary Western ideology of gender binary through dress.
I found that many of the authors wanted to demonstrate the effects of socially constructed gender. In The Boy in the Dress, this meant that the protagonist felt alienated through his family’s masculine reinforcement. Both Walliams’s novel and Blacker’s Boy2Girl, highlight the discrimination towards the cross-dressing male, which illustrates an out of date notion of homosexuality being linked to dress. Twain aimed to deconstruct the gender binary by presenting a character that was not affected by gendered clothing, whilst Grahame used the act of cross-dressing to reinforce gender binaries. Humour was a trope in all of the novels which was a result of inadequate gender performance, however, this highlighted that gender is socially constructed and therefore, unnatural. Not only did Walliams attempt to deconstruct the notion of the gender binary and demonstrate how emotions are similarly gendered, he also encouraged his reader to believe that clothing is irrelevant to gender. The originality of Walliam’s novel arises from his exploration of feelings surrounding gender and gendered dress and how these restrict individual freedom and result in segregation.
Adams James Eli and Millar Andrew H, Sexualities in Victorian Britain (U.S.A: Indiana University Press, 1996)
Blacker, Terence, Boy2Girl (Oxford: Macmillan Children’s Books, 2004)
Bolich, G.G, PhD. Today’s Transgender Realities: Crossdressing in Context (North Carolina: Psyche’s Press, 2007)
Fischer, Agneta, Gender and Emotion: Social Psychological Perspectives (Cambridge: Cambridge University Press, 2000)
Flanagan, Victoria, Into the Closet: Cross Dressing and the Gendered Body in Children’s Literature and Film (Oxfordshire: Routledge, 2011)
Grahame, Kenneth, The Wind in the Willows (London: HarperCollins Publisher, 1908)
Harrison, Kelby, Sexual Deceit: The Ethics of Passing (Plymouth: Lexington Books, 2013)
Nangeroni, Nancy, in Into the Closet: Cross Dressing and the Gendered Body in Children’s Literature and Film, ed. by Victoria Flanagan (Oxfordshire: Routledge, 2011)
Sedler, Victor J. in The New Politics of Masculinity: Men Power and Resistance ed. Fidelma Ashe (Oxon: Routledge, 2007)
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Twain, Mark, Adventures of Huckleberry Finn (New York: Charles L. Webster and Company)
Walliams, David, The Boy in the Dress (London: Harper Collins, 2008)
 Nancy Nangeroni, in Into the Closet: Cross Dressing and the Gendered Body in Children’s Literature and Film , ed. by Victoria Flanagan (Oxfordshire: Routledge, 2011), p.258.
 Davis Walliams, The Boy in the Dress (London: Harper Collins, 2008), p.11.
 Victor J. Sedler in The New Politics of Masculinity: Men Power and Resistance ed. Fidelma Ashe (Oxon: Routledge, 2007), p.111.
 Agneta Fischer, Gender and Emotion: Social Psychological Perspectives (Cambridge: Cambridge University Press, 2000), p.173.
 G.G. Bolich, Ph.D. Today’s Transgender Realities: Crossdressing in Context (North Carolina: Psyche’s Press, 2007), p.271.
 Kenneth Grahame, The Wind in the Willows (London: HarperCollins Publisher, 1908), p.79-80.
 Victoria Flanagan, Into the Closet: Cross Dressing and the Gendered Body in Children’s Literature and Film (Oxfordshire: Routledge, 2011), p.143.
 Mark Twain, Adventures of Huckleberry Finn (New York: Charles L. Webster and Company), para. 9 of Chapter 10.
 Terence Blacker Boy2Girl (Oxford: Macmillan Children’s Books, 2004), p.44.
 Edwin B. Steen and James H.Price, Human Sex and Sexuality (London: Costable and Company, 1988), p.297.
 James Eli Adams and Andrew H. Millar, Sexualities in Victorian Britain (U.S.A: Indiana University Press, 1996), p.97.
 Kelby Harrison, Sexual Deceit: The Ethics of Passing (Plymouth: Lexington Books, 2013), p.9.