Upon arriving at home one December evening, Matthew discovers Anne with a group of her friends rehearsing for their Christmas assembly. As Matthew watches the girls, he notices that somehow Anne looks different from the rest. He cannot quite put his finger on what makes that difference, but it continues to bother him for the rest of the night. It is not until he has smoked several pipes of tobacco that it finally dawns on him: the other girls in Anne’s group are better dressed. Once he realizes this, Matthew reflects on other memories he has of Anne and the other girls. Anne has always been more poorly dressed than her friends. Marilla has kept Anne clothed in plain, dark dresses that are all made from the same pattern. Although Matthew is not well versed in women’s fashions, he is able to detect a major difference in the sleeves of Anne’s dresses. The other girls also wear bright colors, like red, blue, or pure white. Matthew concludes that Marilla must have her reasons for dressing Anne so conservatively. However, he sees no harm in Anne’s having at least one pretty dress. Matthew decides to buy Anne a present of a new dress.

The next day, Matthew drives into town and goes to Samuel Lawson’s store. Unfortunately, when Matthew enters the store, he finds that the owner has hired a lady clerk. The woman is nicely dressed and wears several bracelets that glitter and “tinkle” with every movement of her wrists. All of these elements confuse and frustrate Matthew. When the woman asks what Matthews needs, he stammers before asking for a garden rake. This is a strange request (it is the middle of December) but the female clerk obliges Matthew by going to the back of the store and pulling out a rake from storage. After requesting the rake, Matthew asks for some hayseed and then twenty pounds of brown sugar. Matthew is so rattled by the woman that he leaves the store without purchasing Anne’s present.

The next day, Matthew decides that it is not a man’s place to buy a young girl’s dress. So he goes to Mrs. Lynde and asks her to please choose and purchase a nice dress for him to give to Anne. Mrs. Lynde agrees to do this. Matthew asks Mrs. Lynde to make sure the dress has puffy sleeves, like the ones the other young girls are wearing. Mrs. Lynde is excited about her task. She thinks Marilla has been negligent in providing decent dresses for Anne. Mrs. Lynde adds to the gift an extra ribbon for Anne’s hair, and Diana’s Aunt Josephine gives Anne a gift of fancy shoes. With the concert a huge success, it is the best Christmas Anne has ever had.