It's always a surprise for a Newbery medalist to be so slim, even when you've read it before!
This book is about Maddie, a young girl who is best friends with Peggy, the most popular girl in school. Lately, Peggy has taken to teasing Wanda, the daughter of an immigrant single father. Generally, Wanda flies under the radar- she sits unnoticed in the back of room 13 and participates as little as possible. But one day she calls attention to herself by mentioning that she has one hundred dresses at home, all lined up in her closet.
Since Wanda appears at school every day in the same clean but tired dress, this claim is a ludicrous one. She seems oblivious to how foolish this sounds coming from her, so Peggy makes a point to wait for her regularly on the way to or from school to ask her about them and praise their descriptions profusely in jest. This makes Maddie uncomfortable, and she never joins in, but she also doesn't dare ask Peggy to stop, either. After all, Wanda has never been brought to tears, so no real harm has been done, and Maddie certainly doesn't want to call attention to her own hand-me-down dresses.
Eventually, the girls notice that Wanda has been absent from school for several days (they have been made late to class by waiting to tease her, but she never passes by). She doesn't even return in time to learn that she was her grade's winner for the girls' drawing contest- the winner was to design the most beautiful dress, and each of Wanda's 100 entries was better than any of the others. Eventually, the teacher receives a letter from Wanda's father. In his own awkward English, he narrates that Wanda and her older brother will no longer be attending school there. Their family is moving to the city, where there are plenty of immigrants with unusual surnames, so they should no longer be mocked. This makes Maddie feel much worse about never having stood up for Wanda, and Peggy is apparently also upset by her role.
The two girls decide to try to find Wanda and make amends, but her home is long since empty. The best they can do is to write her a kindly letter (they can't quite find the words to express their apology) and hope that the post office is able to forward it to Wanda's new home. Months later, at Christmastime, their teacher receives a letter from Wanda, telling that she likes her new home and school, and that she especially wishes for Peggy and Maddie to keep two of her drawings. Upon hanging hers up at home and studying it in more detail, Maddie notices that she herself has been drawn as the wearer of the dress. She rushes over to Peggy's house, and the same is true of Peggy's drawing. They know then that Wanda was fond of them all along, and that their letter was received and all is forgiven.
This one was a great book for kids about the subtle impact of bullying, without getting too preachy or overdramatic. Of course, it was written in a different time when a bully's access to a victim is not as pervasive as it is now. But it allows a young reader to gain empathy under a simpler set of circumstances. Definitely a keeper story.
That said, I know that this book won the Newbery Honor, and not the Caldecott. And I know that Eleanor Estes and Louis Slobodkin appear to have a "thing" (he illustrated most, if not all, of her books in their original edition). But if the main thrust of your book is the beauty of 100 hand-drawn dresses, wouldn't it have been in the publisher's best interest to select an illustrator who would effectively convey this? The cover shown above reflects all of the book's illustrations. They're hardly awe-inspiring.
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