Our Top 10 Favorite Caldecott Winners

My kids and I just finished reading through every single Caldecott winner from 1938 through the present! We have been working on this project slowly over the last several months (thank you, quarantine!), and it was exciting to finally finish!

We have talked and looked through this list pretty extensively and have come up with our top 10 favorite Caldecott-winning books. We LOVED all ten of these and would absolutely recommend that you own them (affiliate links below).

A few notes as I reflect on our Caldecott journey:

1. My kids read all of these with me and range in age from 3-10. While the Caldecott winners are chosen specifically for their illustrations, the story itself obviously also matters to us — so our ratings are based on both the storyline and illustrations.
2. I was so impressed and excited by how diverse these books are. We traveled to a train station in Paris, a Russian peasant village, 20th century Japan, multiple African villages, a Pueblo Indian settlement, a Scottish manor, a Mexican posada, and a Chinese fair, just to name a few. Main characters are African, Hispanic, Asian, American, European, and almost everything in between.
3. If you ever complete this project yourself, it is fascinating to watch the progression of history and style throughout the books. While most of these I would consider “timeless” in some sense, the style of language and illustrations changed drastically through the years.
4. If you’re curious to know our ratings of each of the Caldecott winners, you can see those here.

With no further ado… our top 10 Caldecott Winners!

10. Officer Buckle and Gloria (1996)

This was a particular favorite of my 8-year-old daughter, who first read it in school before insisting we check it out from the library and reading it again at home. Well-meaning Officer Buckle gives very boring safety presentations to elementary students until his dog, Gloria, begins to steal the show — but Officer Buckle still thinks all of the cheers and attention are for him. Wonderful illustrations and truly a humorous, cute storyline.

9. One Fine Day (1972)

This was one I had never even heard of before, but we loved every page! Based on an American folktale, it tells the story of a fox who loses his tail and must go on a very circuitous journey to get his tail back. If you love “The Napping House” or “If You Give a Mouse a Cookie,” you will love this one for the repetition and interconnectedness of all of the story’s events.

8. Make Way For Ducklings (1942)

How could we not include this classic that has been so loved for so many generations? Robert McCloskey is brilliant (he also won the Caldecott for “Time of Wonder,” which was wonderful), and this lovable tale of a duck family finding their way to a new home in the Boston Public Gardens is great for all ages. Now we just can’t wait to visit Boston as a family one day to visit all of the sites we’ve read about in this book!

7. Joseph Had a Little Overcoat (2000)

While I love picture books of varying lengths, probably my favorite ones are those short enough to keep the attention of a 2- or 3-year-old. This one fits that description, but it is also fun and engaging enough to keep the attention of my older elementary kids. As Joseph’s overcoat wears down over time, he keeps repurposing it into smaller and smaller articles of clothing until it is just about gone — and he learns you can always make something, even out of nothing.

6. Ox-Cart Man (1980)

I have to be honest and say this one ranks so high on our list because it might be my very favorite Caldecott winner of all! The story follows a 19th-century New England family through the changing seasons of a year of their lives, as they produce goods and then go to market to sell them. The illustrations are fantastic, and it teaches a great deal about rural New England life in a subtle, beautiful way.

5. A Sick Day for Amos McGee (2011)

Every day Amos McGee goes and spends time with all of his animal friends at the zoo, until one day he doesn’t show up because he is home in bed with a cold. What he doesn’t expect is that his animal friends will find their way to him to make sure he is well taken care of! What I love about this book its celebration of a very ordinary man who realizes how strong his impact is when he isn’t able to show up.

4. This Is Not My Hat (2013)

My 5- and 3- year-old cannot get enough of this book! It is short, funny, and simple, but there is something about it that just captivates my little guys. A tiny fish has stolen a hat from a huge fish, and he spends the book convincing himself that he won’t be caught — even though the reader sees that he isn’t quite as safe as he thinks he is.

3. The Invention of Hugo Cabret (2008)

I had only heard of this book because of the movie Hugo, and I was a bit shocked when we checked it out from the library to find it was more than 500 pages long! However, more than half of those pages are illustrated because it combines elements of both literature and cinema as it tells the story of an oprhan boy who keeps the clocks in a Paris train station. We listened to the audio book (which includes sound effects on the illustrated pages) and followed along with the hard copy of the book at the same time, and it made the story even more enthralling!

2. The Snowy Day (1963)

Pulling out this book about a young boy’s experience playing in the snow is like catching up with an old friend. I’m not sure whether it’s the magical illustrations, the simple but meaningful storyline, or just the relatability of the joy of playing in snow, but all four of my kids have asked for this book over and over and over again through the years.

1. Finding Winnie (2016)