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Stuff for the Teen Age

Girls in Pants: Girls Disguised as Boys


The idea of girls masquerading as boys to infiltrate the male world is not new; in fact, it's a literary staple. From William Shakespeare to Amanda Bynes, all it takes is some cloth to bind and flatten the chest, short hair, a lowering of the voice, some rolled up socks artfully placed, and voila — a boy is born! Of course, it also helps if there is a clueless boy who befriends the masquerader and then suddenly begins to question his sexuality when he wants to kiss the girl in disguise. And, to make things even more complicated, another girl arrives on the scene. Mistaken identities, mistaken crushes, and crazy hijinks ensue, and fun is had by all!

You could say that girls disguised as boys was one of Shakespeare's favorite plot devices, as it appears in several of his plays: Twelfth Night, As You Like It, Two Gentleman of Verona, Cymbeline, and The Merchant of Venice. Perhaps for Shakespeare it was expedient. After all, no females were allowed on the Elizabethan stage, so all femail roles were played by young male actors in drag; therefore, a girl disguised as a boy could be very convincingly played by a boy disguised as a girl!

Girls disguised as boys is also a favorite plot device in teen fiction. Throughout history girls have been denied the same freedoms, opportunities, and adventures as boys, and so in all fictional genres one finds girls disguised pirates, highwaymen, knights, soldiers, pilots, dragon keepers, or sports players to get an education, get the inside scoop on being a boy, or keep safe in a male dominated world — just to name a few.*

Babe in Boyland (2011) by Jody Gehrman

In this fun and thought-provoking modern romance, Natalie is the romance columnist for her school newspaper. When her love advice, written under the pseudonym "Dr. Aphrodite," is ridiculed by the boys as being unrealistic and strictly for "girls only," Natalie decides to do some investigative reporting on what boys really think and want. However, the boys at her school won't open up to her. Her solution? Go undercover at the local all boys boarding school! A little computer hacking, a haircut, some makeup, and a ball of socks, and "Nat" is good to go. The plot gets a little absurd when she falls for her roommate Emilio, gets a reputation for being a "player," and almost gets caught several times — some of her exits and entrances at one point are farcical. While not ground-breaking, Natalie's conclusions about boys, girls, and relationships give the reader plenty to think about when it comes to the opposite sex, and there are lots of laughs along the way.

The Education of Bet (2010) by Lauren Baratz-Logsted

In this 19th century tale, Bet (short for Elizabeth) and Will are both raised in luxury by Will's great-uncle. However, unlike Will who is allowed to go to school and have all sorts of adventures, Bet is stuck in the country learning needlepoint and other skills to make her a good wife. The irony is that Will is a horrible student and Bet is smart and clever. When Will decides that he would rather join the army, Bet hatches a plan that has her impersonating Will at his new boarding school. Bet is horrified by the brutality of the all boys school but exceeds in classes and fights off the bullies with the help of her handsome, charming roommate James (ahem). While there is not a lot of depth, this is a fast, fun, historical read with an appealing heroine. My one complaint is that it is too short and too quick of a read. I reached the end and said, "thats it?" And not because it wasn't satisfying, but because I wanted to continue following Bet's adventures.

More Masquerading/Gender-Bending Tales: In addition to the books and plots already mentioned above, there are many, many more books out there. With this list, I am only scratching the surface:

  • Bloody Jack (part of a series) by L.A. Meyer — historical fiction
  • Alanna, The First Adventure (part of a series) by Tamora Pierce — fantasy
  • Sovay by Celia Rees — historical fiction
  • Leviathan (part of a series) by Scott Westerfeld — steampunk fantasy
  • Eon (part of a series) by Alison Goodman — fantasy
  • Yentl, the Yeshiva Boy by Isaac Bashevis Singer — folk tale
  • The Agency (part of a series) by Y.S. Lee — historical crime fiction
  • The Blue Sword by Robin McKinley — fantasy
  • Ouran High School Host Club (part of a series) by Bisco Hatori — manga
  • Girl in Blue by Ann Rinaldi — historical fiction
  • Daughter of Venice by Donna Jo Napoli — historical fiction
  • Graceling by Kristin Cashore — fantasy
  • The Wild Orchid by Cameron Dokey — ballad retelling
  • Princess Ben by Catherine Gilbert Murdock — fantasy
  • Pirates! by Celia Rees — historical fiction
  • The Folk Keeper by Fanny Billingsly — fantasy
  • Hana Kimi (part of a series) by Hisaya Nakajo — manga
  • Gender Blender by Blake Nelson — This is more Freaky Friday than girl disguised as boy, but it is one of my all time favorites! Two on-the-outs friends in seventh grade switch bodies via a Native American artifact. Being a girl in a teen boy's body has never been more disturbing or confusing!


I was actually inspired to write this post after remembering a favorite 80s film, Just One of The Guys, which is currently NOT available on DVD and thus very upsetting to me (see picture at top)! So that got me questioning, what else is out there? The very good Amanda Bynes's film She's The Man comes to mind. It also stars a very cute and confused Channing Tatum, so its not to be missed! That film is heavily based on Shakespeare's Twelfth Night, and my favorite film adaption of that play stars Toby Stephens and Helena Bonham Carter (see below). Let's not forget Barbara Streisand in Yentl or the protagonist in Disney's Mulan, who helped defeat the Huns and save the Emperor. And when it comes to inspiring masquerade tales, it's the true story of Joan of Arc (this film-bio stars Leelee Sobieski). I also want to do a shout out to a short-lived WB TV series from 2000, Young Americans. A spin-off of Dawson's Creek, one plot line starred Ian Somerhalder (The Vampire Diaries) as a boarding school student who's roommate is masquerading as a girl. You can find all eight episodes of the show on DVD and YouTube.

So what have I NOT listed here? Let's keep this list going:

*You've probably noticed that I haven't listed any LGBTQ titles featuring transgender girls. I feel that those titles warrant their own list and have decided not to include them on this blog post.


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Girls in Pants

There are plenty of girls disguised as boys in historical fiction, reflecting the limitations placed on women throughout history... In Nobody's Princess by Esther Friesner, Helen (who will become Helen of Troy) learns to fight, hunt, and ride horses while disguised as a boy, and goes on an adventure throughout the Mediterranean world. In The Breadwinner by Deborah Ellis, 11-year-old Parvana disguises herself as a boy in Taliban-controlled Afghanistan to save her family after her father's arrest. And in Fan Dai's Butterfly Lovers: A Tale of the Chinese Romeo and Juliet, a young girl disguises herself as a man and lives with a male scholar for three years before her passion for the young man gets the best of her.

Mr. Headmistress

Mr. Headmistress is a funny movie about a conman who disguises himself as the headmistress of an all -girls school

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