The third chapter continues following Maddie’s point of view. On the Wednesday morning that she notices Wanda is not at school, Maddie finds herself unable to focus on her schoolwork. She carefully sharpens her pencil and frowns. She is displeased with herself for having arrived late to class, but she is also thinking about Wanda; Wanda’s empty desk seems to be the only thing Maddie can see when she looks behind her.
Maddie tries to recall how the hundred dresses game began. The narrative shifts to Maddie’s memory of that day: It had begun the morning when Cecile first wore her new red dress. It was a bright blue day in October. Peggy and Maddie had been walking with their arms linked with the morning sun shining in their eyes. Maddie saw flashes of color from the clothes on a group of girls across Maple Street. Cecile’s crimson dress caught the sunlight like a bright piece of glass.
Maddie and Peggy joined the group and everyone admired Cecile’s elegant clothing. Maddie remembers how jolly everyone was, and how all the colors seemed to sparkle in the brilliant sunlight.
Wanda and her brother Jake approached on their way to school. Jake must have been late; he didn’t normally walk with Wanda because he had to come to school early to help the janitor, Mr. Heany, with odd jobs before the school opened. Even Wanda was pretty in the sunshine, her pale dress looking like a piece of summer sky.
Maddie heard Jake say that he had to hurry to school to open the doors and ring the bell, but Wanda said she wanted to stay there on Maple Street. Jake left while Wanda approached the group of girls, first hesitating for a long time, like a timid animal. Nonetheless, Wanda twisted her mouth into a smile.
Wanda joined the group, which grew larger as more girls arrived to admire Cecile’s new dress. Wanda was part of the crowd, but no one was talking to her, nor thinking about her. Maddie speculates that perhaps Wanda thought she could be accepted by the group if she joined in the talk about dresses. Wanda impulsively touched Peggy’s arm and said something softly, her light blue eyes shining with excitement. Peggy asked Wanda to repeat what she’d said, and, after hesitating, Wanda said that she had one hundred dresses at home.
Peggy loudly mocked Wanda for saying something so implausible. The other girls turned from Cecile to question Wanda. When asked why she didn’t wear the dresses to school, Wanda drew her lips together and simply repeated that she had a hundred dresses, all lined up in her closet.
The girls ran off laughing to school when they heard the first warning gong. From then on, Peggy teased Wanda about the hundred dresses to make the other girls laugh. The teasing happened so quickly that Maddie, even though uncomfortable, couldn’t do anything to stop it.
The narrative returns to the present, with Maddie nodding to herself, saying that’s how it started, with the bright blue day in October. She then takes her pencil shavings to the teacher’s wastebasket at the front of the room.
In the third chapter, the narrative point-of-view stays with Maddie as she recounts the day the "hundred dresses" game began. In Maddie’s recollection, the day began by being filled with positive energy, due to how the bright sunshine made colors appear especially brilliant and sparkly. To illustrate the beauty of the colors, the author uses a simile to compare the girls’ dresses to pieces of colored glass.
Wanda’s brother Jake is introduced as a character; the reader learns that Jake, though a student, comes to school early to work with the janitor. This detail hints at the need for money in the Petronski household, and signifies Wanda’s and Jake’s lower class status.
The narrative touches on the theme of social isolation when Wanda attempts to join the group of girls who are admiring Cecile’s red dress. Wanda’s manner is awkward: as she hesitates to join the group and then stands in silence, it is clear that she is unaccustomed to social interactions. The image of her shining eyes indicates Wanda’s hope at being included in the group.
As Maddie recalls, Wanda’s grave error was to tell Peggy she had one hundred dresses at home. Wanda’s social awkwardness means she is unable to predict the ridicule she will receive for making such an outlandish claim. From this point on, Wanda was doomed to schoolyard taunts.
Maddie regrets not having intervened before the hundred dresses game began, but the excitement it caused for the other girls meant the game’s momentum was impossible for Maddie to stop on her own. It is significant that Maddie has been sharpening her pencil while thinking about Wanda; the action foreshadows how Maddie will eventually write a letter to Wanda to convey her remorse.