Content Warning: This section of the guide includes discussion of racism.

Samantha and Annamae are aware from the start of their journey that, as girls traveling alone, they are vulnerable and noticeable. They want to travel safely, but they also want to travel invisibly because they are both being pursued by the law. They decide to disguise themselves as young male teenagers. This means that they must not only deal with the physical challenges of disguising themselves as male, but also the emotional and social aspects that are involved in the gender expectations of the 19th-century American West. Lee often presents these expectations as binary differences between males and females: Men and boys are meant to be brave, strong, and independent, while women and girls are meant to be frightened, weak, and submissive. Samantha and Annamae negotiate these challenges, and through their actions, Lee draws attention to the performativity of gender roles.

Each girl faces different challenges when disguising herself as a boy. By discussing these challenges, which frequently revolve around biological attributes, Lee demonstrates how 19th-century gender roles are tied to one’s sex. For Annamae, the main problem lies in binding her breasts with a ribbon. Lee also mentions more intimate issues, such as menstruation, bathing, and calls of nature.