On a cold December evening, Matthew enters the kitchen and realizes too late that Anne and her friends are already there conducting a rehearsal of “The Fairy Queen” in preparation for the Christmas concert. Shy of all the little girls, he stays silently in the corner until they leave. While observing the group, Matthew notices that Anne is dressed differently from her friends. He becomes convinced that she needs more fashionable clothing and goes into the town of Carmody to find a bright dress with puffed sleeves. Shopping is not an easy task for such a shy man, but Matthew summons his courage and goes to Samuel Lawson’s store, which he thinks will not have a female clerk at the desk. Much to Matthew’s dismay, he finds that Samuel Lawson has hired a female clerk, Miss Lucilla Harris.
Matthew is too scared to ask Miss Harris for fashion advice, and asks for twenty pounds of brown sugar and a garden rake before making his escape. Matthew eventually asks Mrs. Rachel for help, and she picks out a rich brown fabric and uses a fashionable pattern to make Anne’s dress. Mrs. Rachel has often wondered why Marilla dresses Anne so plainly and is happy to have a part in updating Anne’s wardrobe. On Christmas Day, Matthew unveils the dress, complete with puffed sleeves. Diana comes over with a present from Aunt Josephine for Anne: delicate slippers. Anne is delighted by her beautiful new garments.
Anne’s Christmas concert is the first one Matthew and Marilla have been to in twenty years. Anne, wearing her new dress and shoes, is the star of the show. Both Cuthberts are swollen with pride. Matthew immediately tells Anne how proud he is of her, but Marilla decides not to compliment Anne.
After the excitement of the Christmas concert, the Avonlea students return to their normal, humdrum patterns. Anne, now almost thirteen, vows to improve herself by imitating Mrs. Allan, refraining from saying uncharitable things and trying to do good.
For school, the students are assigned to write a piece of fiction and a composition about a walk in the winter. These assignments displease Marilla because they rely on imagination rather than memorization. They elate Anne, however, and she completes her original story early. Diana moans that she does not have enough imagination to do the assignment. To help Diana cultivate her imagination and to practice her own writing, Anne proposes that the two girls start a story club. Two of their friends, Jane Andrews and Ruby Gillis, eventually join, and the girls spend their time inventing romantic, melodramatic storylines.
One evening in late April, Marilla walks home feeling uplifted and lighthearted, though she does not realize that the sights of spring are the cause of her joy. She happily anticipates the warm fire and tea that Anne should have prepared for her at home. When she reaches Green Gables, Marilla finds the table bare and Anne nowhere to be found. She complains to Matthew that Anne has disobeyed her order to stay at home and prepare the meal. Her anger turns to concern when suppertime comes and there is still no sign of Anne. Marilla goes upstairs to get a candle from Anne’s room and finds her lying facedown on her bed, moaning that she is too ugly to be seen. It turns out that Anne has dyed her hair with disastrous results. She bought hair dye from a traveling peddler who claimed the dye would turn her hair raven black. The dye turned her hair green, and the only solution is for Marilla to crop it to an unfashionably short length. At first Anne weeps at the sight of herself in the mirror, but she then decides to look at her unattractive reflection to remind herself of the folly of vanity.
Anne, Diana, Ruby, and Jane enact a scene from a poem by Alfred Lord Tennyson in which the corpse of a character named Elaine is sent down a river in a barge. Though Anne does not look like Elaine, who has golden hair, she gets the part because none of the other girls want to drift down the pond alone in Mr. Barry’s little boat. The girls recite romantic farewells and send Anne’s unmoving body down the pond. For a few minutes, Anne revels in the romance of the situation, but she then feels water at her back. The boat has a leak, but Anne remains calm and prays for God to bring the boat close to one of the bridge piles (poles running vertically from the bridge to the bottom of the river) so she can grab on and wait for help. The girls see the boat sink, and, thinking that Anne has sunk with it, they run screaming for help. Anne is able to get to a bridge pile, however, where she hangs on and waits uncomfortably for help.
Just when Anne begins to think she cannot hold on any longer, Gilbert Blythe rows up and rescues her. After depositing her safely on the bank, he makes a friendly overture, apologizing again for calling her “Carrots” when they first met and complimenting the auburn color her hair has become. For a moment, Anne hesitates and considers befriending her sworn enemy. But she then recalls her humiliation during the “Carrots” incident and declares she will never become friends with him. Gilbert storms off. Meanwhile, Diana and Jane cannot find any adults to help and have become frantic. Ruby, always inclined toward hysteria, grieves at the Barry house. When Diana and Jane return to the pond, they are relieved that Anne is safe and thrilled by the romance of her rescue by Gilbert. Anne, however, orders Jane never to say the word “romantic” again.
To some extent, Matthew and Marilla reverse the characteristics traditionally associated with men and women. Matthew goes to great trouble to get Anne a new, fashionable dress, exhibiting almost womanly qualities. Whereas Marilla thinks fashion silly, Matthew understands that Anne’s dowdy dresses probably embarrass her; he sees the importance of fitting into one’s peer group. Whereas Marilla is reserved and does not believe in spoiling children, exhibiting almost manly qualities, Matthew easily expresses his affection for Anne and welcomes every opportunity to dote on her.
Anne’s approach to writing, which she describes in Chapter 26, reflects Montgomery’s own approach. Anne writes romantic stories about ladies named Cordelia and Geraldine who fall in love and meet tragic ends. She explains to Marilla that the stories all have morals: the good people are rewarded and the bad people are punished. Similarly, Montgomery makes moral judgments about Anne’s behavior. Montgomery does not divide the world into good and bad people, but she does reward Anne’s strengths and punish her faults. Anne’s mistakes never result in tragedy, but she meets with difficulties that are tragic in her perspective.
At the end of Chapter 28, Anne reflects on all of her mistakes. She realizes that each mistake has taught her an important lesson and that, taken together, the mistakes and lessons have made her a better person. After taking Marilla’s brooch, for example, she learns not to play with things that don’t belong to her. After running panicked through the woods, she learns to keep her imagination in check. After making cake with liniment, she learns to take care while cooking. After dyeing her hair, she learns to curb her vanity. Anne’s faults and quirky traits, which Marilla and Mrs. Rachel enumerate at the beginning of Anne’s stay, disappear with every mistake, chapter by chapter.
Although Anne’s desire to rid herself of faults shows her maturation, she has not yet perfected herself. For example, she resolves to be modest after her vanity results in green hair, but her vanity over her hair makes her simmer afresh over a years-old insult and causes her to reject Gilbert’s offer of friendship. Gilbert’s rescue teaches Anne yet another lesson that demonstrates that she still has room to mature: real-life romance does not yet suit her. Although the boat episode has all the markings of the kind of fictional romance Anne loves—danger, a woman in distress, a last-minute rescue by a handsome man—Anne finds the event awkward, embarrassing, and irritating rather than charming and romantic.