Simsion uses clothing to describe his characters’ attitudes and their roles in society. Don constantly describes both his own clothes and other people’s in great detail, frequently noting colors, styles, textures, and accessories.

Don constantly refers to people’s clothing choices as costumes. In this way, he reveals that he finds all forms of dress to be social play-acting—people dress according to their roles in life’s play. This attitude highlights Don’s contempt for social custom. As a result, he rarely dresses like a conventional adult, choosing instead to dress for functionality no matter the situation.

However, while Don claims that he pays little attention to his appearance, his constant references to dress and its social appropriateness, or lack thereof, reveal his preoccupation with social correctness. He is pretending to be dismissive because his initial attempts to dress appropriately were so outside the norm that they brought him only ridicule. As the novel progresses, he seeks advice to gain the expertise he lacks—how to dress in a way others would consider appropriate for his age and role in life. Don’s outer transformation into Gregory Peck, to attract Rosie, symbolizes his inner transformation and the role Rosie plays in it. 

Both Don and Rosie call attention to themselves through non-traditional clothing choices. Rosie has an intentionally unique look that reflects her independent spirit and feminism. Her glasses, hair color, and choice of attire—frequently punk or Goth-influenced—make a deliberate statement; for example, she consciously chooses to dress in a manner that communicates disinterest in male attention. Rosie, however, can conform when she wants to because she has a more sophisticated understanding of social mores. For example, she wears a pretty ball gown to the faculty ball, and she enjoys choosing a gorgeous, expensive scarf for Claudia in the Hermes shop in New York.