The best illustrated children’s books for parents and kids to read together

The Books I Picked & Why


By A.A. Milne, Ernest H. Shepard

Book cover of Winnie-the-Pooh

Why this book?

Most people know Winnie the Pooh from cartoon adaptations, but those have never done justice to the original stories. Milne’s characters are incredibly funny and human, putting themselves in ridiculous situations and attempting to solve problems with even more ridiculous solutions, all with the seemingly nonsensical logic of a toddler. While kids may enjoy Pooh’s antics for their sheer silliness, adults will appreciate the subtle commentary on grown-up foibles and love the deep heart with which Pooh navigates the world.

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By René Goscinny, Jean-Jacques Sempé

Book cover of Nicholas

Why this book?

Although there are some parts of the Nicholas series that don’t hold up quite as well today – Nicholas and his friends attempt to smoke a discarded cigar, and their game of cowboys is extremely dated – these everyday adventures perfectly capture the feeling of being a kid looking out at a world that doesn’t make sense, because the world is run by grownups. Narrated by Nicholas himself, each chapter is a self-contained story full of the hilarious ups and downs of childhood. Sometimes when you’re a kid, no matter how hard you try to do good, you still get in trouble, and sometimes, your parents are endlessly frustrated, while you remain happily oblivious.

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Pippi Longstocking

By Astrid Lindgren, Lauren Child

Book cover of Pippi Longstocking

Why this book?

I missed out on reading this as a kid, I think because I saw part of the 1969 movie version and found it unwatchable. But better late than never! A precocious and heroic girl living alone, Pippi Longstocking’s surreal but often literal take on the adult world exposes contradictions and paradoxes in the most entertaining fashion. She behaves the way kids often wish they were allowed to and suffers no fools along the way.

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The Phantom Tollbooth

By Norton Juster, Jules Feiffer

Book cover of The Phantom Tollbooth

Why this book?

There is a lot going on in The Phantom Tollbooth, making the annotated edition well worth reading, but at its core it’s simply another fun book that follows a kid (and his canine companion, an actual watch-dog) on fantastic adventures. There’s literally plenty of literal literary turns of phrase, and the playful language adds layers and levels to the humor. Kids (and even adults) may not understand it all, or all the same, but the humor carries the reader on nonetheless.

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Frog and Toad: A Complete Reading Collection

By Arnold Lobel

Book cover of Frog and Toad: A Complete Reading Collection

Why this book?

There may not be a simpler book that paints a more complex picture of friendship as Frog and Toad. The chapters would be the perfect length for bedtime reading if the two amphibians weren’t so engrossing that both you and your young one will keep deciding on “just one more” until you’ve read them all. Frog and Toad are clever, and naïve, and sweet, and always funny.

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