Cross-dressing as a literary motif is well attested in older literature but is becoming increasingly popular in modern literature as well. It is often associated with character nonconformity and sexuality rather than gender identity.
Analysis and function of the motif
Female characters who cross-dress as men are also frequently portrayed as having done so to attain a higher social or economic position, a phenomenon known as the social progress narrative. Assuming a male identity allows them to travel safely, pursue jobs traditionally only available to men, and find heterosexual romance by breaking away from the all-female social world of the private sphere during the nineteenth and early twentieth centuries. These characters are generally described as heroic, courageous, and virtuous. Craft-Fairchild (1998) argues that the motif of female-to-male cross-dressing symbolizes women’s discontent with their relegation to the domestic sphere of society. However, the discovery of the characters’ assigned sex is often met with disapproval, indicating the endurance of traditional expectations of femininity.
Male-to-female cross-dressing is much less common in literature, and it is often used for comedic value or as a form of punishment for a male character. When it does appear, characters are often negatively feminized or portrayed as villains, in contrast to the heroism among female-to-male cross-dressers. The most well known example of this concept is the wolf from Little Red Riding Hood. Male-to-female cross-dressing is also almost always more closely linked to a character’s sexuality and that of their partners than in female-to-male cross-dressing.
The following is a partial list of literary works that address the motif of cross-dressing:
Ancient and medieval literature
Achilles on Skyros (Achilleid, 1st century)
Roman de Silence (13th century)
Þrymskviða from the Poetic Edda - Thor dresses as a bride and Loki as the bridesmaid to retrieve Thor's hammer Mjölnir.
Several of William Shakespeare's works include cross-dressing
The Merchant of Venice (c1657) a play by William Shakespeare in which Portia dresses as a man in order to defend Antonio against Shylock's suit for the 'pound of flesh' he is owed as forfeiture for failing to repay a debt in time.
Cymbeline (c1611) in which Cymbeline's daughter Imogen dresses as a page and calls herself "Fidele".
Belle-Belle ou Le Chevalier Fortuné (1698) - a fairy tale by Madame d'Aulnoy in which the female protagonist, Belle-Belle, disguises herself as a male knight to help the ruler of her kingdom defeat an emperor.
Edmund Spenser's "The Faerie Queene" includes a long section about Britomart, who dons male armor, falls in love with a woman, and has many adventures as a man.
Mademoiselle de Maupin by Theophile Gautier (1834) in which the eponymous heroine dresses as a man to discover what men are like when not in the company of women before she gets married.
The Masqueraders, by Georgette Heyer (1928); historical novel. Two siblings impersonate the opposite gender to escape persecution after the 1745 Jacobite Rising.
These Old Shades by Georgette Heyer; historical novel. During the reign of Louis XV, a girl disguises herself as a boy.
The Famous Five book series (1942) - Georgina wears boy's clothes, prefers to be called "George" and is pleased to be mistaken for a boy.
The Rose of Versailles (1972) - The female protagonist, Oscar François de Jarjayes, dresses as a man, but privately acknowledges her feminine side.
Johnny, My Friend (a translation of the Swedish novel Janne, min vän from 1985) - Johnny is a girl disguising as a boy.
Song of the Lioness - The main character, Alanna, disguises herself as a boy to become a knight.
Soldier's Secret - A fictional retelling of Deborah Sampson's life, who disguises herself as a soldier during the Revolutionary War.
Hana Kimi - A Japanese Manga, where the female protagonist, Ashiya Mizuki disguises herself as a boy to attend an all-boys school where her idol Sano Izumi attends.
Boy2Girl by Terence Blacker - Sam, the main character Matthew's male American cousin, is dared to go to school disguised as a girl as a challenge to prove himself to Matthew and his friends. However, the prank doesn't turn out the way it was planned.
The Outlaws of Sherwood (1988) by Robin McKinley - A young girl disguises herself as a boy and joins Robin Hood's band of outlaws.
Rowan Hood: Outlaw Girl of Sherwood Forest (2002) by Nancy Springer - A girl dresses as a boy to find her father, the famous outlaw Robin Hood.
Ouran High School Host Club series by Bisco Hatori - a female student masquerades as a boy to earn extra cash.
Princess Princess series by Mikiyo Tsuda - a young male student is invited to join an elite club at his new school whose members dress like girls.
Monstrous Regiment (2003) by Terry Pratchett - After her brother vanishes, Polly Perks dresses up like a man to find him.
Leviathan (2009) by Scott Westerfeld - Deryn Sharp, a young girl, dresses up like a man so she can join the British Air Service.
The Pearl that Broke Its Shell (2014), a novel by Nadia Hashimi - Rahima, an Afghani girl in 2007 needs to adopt the ancient custom of bacha posh that allows girls to dress and be treated as boys until they are of marriageable age in order to take care of herself and her sisters. A century earlier, her great-aunt, Shekiba, left orphaned by an epidemic, saved herself and built a new life the same way.
Yentl and the Yeshiva Boy (1983) by Isaac Bashevis Singer - A young Jewish girl in Poland dresses and lives as a man in order to study Talmudic Law.
Jane Eyre (1847) - Mr Rochester dresses as a Gypsy woman.
Adventures of Huckleberry Finn (1884) - Huckleberry dresses as a girl and calls himself Sarah Williams.
The Two Towers (of The Lord of the Rings) (1954) - Éowyn disguises as the man Dernhelm and travels with the Riders of Rohan to the Battle of the Pelennor Fields.
To the Hilt (1996), a crime novel by Dick Francis. The protagonist hires a young private detective who is skilled in disguise, mainly disguising himself as a woman.
The Wind in the Willows (1908) by Kenneth Grahame - Toad escapes from prison dressed as a washerwoman.
The Black Arrow: A Tale of the Two Roses (1888) by Robert Louis Stevenson - Joanna Sedley is disguised as a boy by Sir Daniel so he can marry her without interference.
