I came across these two books where the (female) main character dresses up like a boy to "infiltrate" a boys' school: Babe in Boyland by Jody Gehrman and The Academy by Emmaline Andrews.
So of course, my immediate thought was the 1985 movie, "Just One of the Guys".
Now, for some crazy reason, you may not want to read 2 YA books about crossdressing. So, I decided to take one for the team (of readers) and read both of them to let you know which one is most worthy of your limited reading time. Since nothing says high school girl who's a crossdresser like this movie, the winner needs to come closest to the spirit of this movie. Because I've seen it 20 times and consider it to be the Gold Standard of anything to do with teenage crossdressing girls.
1. It needs to be a comedy- of course. Can't help it. Because of this movie, I expect hilarity to ensue once a girl cuts her hair and dons a jock strap. I mean, a girl pretending to be a boy? How's she going to pee, or shower, or handle a PE class of "shirts and skins" basketball where she gets to be "skins"? I mean these are opportunities for comedic gold, right? Um, not in the "The Academy" where these things are occasions for beatings, a knife fight, and an attempted rape. Which, because of my movie memories, was not what I was expecting. Winner: "Babe in Boyland" for being a light, funny read.
2. The "Just a Girl" Effect:
I mean, there needs to be a (good) reason why a girl would want to pretend to be a boy, right? Why else would you cut your hair, wear ugly shoes, and have to use the boys' bathroom. I mean, a boys' public bathroom? It's got to be in the Top 5 Most Disgusting and Smelly things in the world.
3. Put a Sock in It:
The Overall Winner of the "Battle of the Crossdressers", is obviously "Babe in Boyland". It won all categories and deserves this: (from the movie, of course)
But, does "Boyland" too closely resemble "Just One of the Guys"? You know, kind of. As I was reading it, I almost felt like some scenes were lifted straight out of the movie. Like the author had also seen the movie 20+ times like me. But in the end, I thought that "Boyland" was overall charming and entertaining enough in its own right. Now "The Academy" deals with more of the darker issues- like gender identity- than "Boyland". But I honestly don't think it presented those well- it felt awkward. Which makes its sinister tone, kind of pointless. Overall, I'd give "The Academy" a 2 star rating, and "Babe in Boyland" a 3 to 3 1/2 star rating.
Jody Gehrman's Website
Add "The Academy: