One of my favorite tropes of all time is when a girl disguises herself as a boy for the purposes of infiltration. It’s hard to articulate why I love this concept so very much, but I do. For me, a woman fooling the patriarchy has a feeling of justified espionage. I have always loved the idea of spying but been a little turned off by its associated questionable morality. These girls are disguised out of necessity, because they cannot achieve their goals any other way. A girl-disguised-as-a-boy is the ultimate outsider, trying desperately to join a group that by her very nature is ultimately impossible. She can give me voyeuristic insight into the guarded interactions of the male of the species – those mysterious creatures.
From a storytelling perspective, our female protagonist’s initial desperate act of subterfuge gives rise to the constant tension of possible discovery. How will friends, colleagues, and superiors react to being duped when she is found out? For the reader knows that she will, eventually, be found out. That constant stress on the character translates, at its best, to an intrinsically thrilling read.
Here are five great books where a girl dresses as a boy or, if you prefer, a woman dresses as a man.
Alanna: the First Adventure by Tamora Pierce
The first in the Lioness quartet; a classic epic fantasy series for young adults. Alanna wants nothing more in life than to be a knight, so she disguises herself as a boy and travels to her nation’s capital to become a palace page. Alanna is witty, stubborn, brave, and talented, but also flawed in such a way that it is all too easy to see why she conceived of this madcap plan and why she might fail.
Sword Masters by Selina Rosen
The story of a woman with a very particular set of skills, and some seriously dangerous secrets, who infiltrates not only a school for swordsmen but a foreign culture, in an effort to build alliances and defeat a common enemy. Disguised as a man she is forced, eventually, to marry a woman, and must face the consequences of her own lies on a personal, as well as a professional, level.
The Price of the Stars by Debra Doyle & James D. MacDonald
The first book in a sprawling space opera trilogy. Beka fakes her own death and becomes Tarnkeep, a thoroughly unpleasant space pirate, in order to unravel the twisting political coils that are tightening the noose of responsibility around her reluctant neck. Beka loves being her male alter ego, and there is a definite aspect of transgender to Beka’s personality, which is neither empathized nor criticized. When Beka is Tarnkeep she is described in 3rd POV as a he, a narrative trick that forces the reader see him for what Beka also is, male. Tarnkeep allows Beka access to freedom, places, people, and information she could never have as her other self. He also finds it much easier to kill. Thus we are never certain if Beka loves being Tarnkeep for what he can give her, for what he is innately, or if she/he simply exists comfortably as two distinct personalities.
To Play the Lady by Naomi Lane
The first book in a (sadly) unfinished series. It features many of the things I love about a girl playing a boy, although in this story our low class tomboy from another culture must play at being both a noble lady and a stable lad. Politics force Jenna to assume this double act, hiding her magical abilities and her manly skills. If discovered, Jenna will bring shame and destruction down upon her family, her nationality, and her entire social caste. For Jenna, the stakes are very very high indeed.
Newt’s Emerald by Garth Nix
A charming take on gaslight fantasy, and uses the girl-disguised-as-boy trope in its more light-hearted guise. In regency times, Newt must track down a missing emerald. As it is much easier to get around alone as a mustache-wearing man, Newt dons the mustache with gusto. Hijinks and a very confused romance result.
New York Times bestselling author Gail Carriger writes comedic steampunk mixed with urbane fantasy in three series: two adult, the Parasol Protectorate and the Custard Protocol, and one YA, the Finishing School series. (And yeah, these feature a popular female side character who dresses as a boy.) Gail was once an archaeologist and is overly fond of shoes, tea, and women dressed as men.