12 Helpful Back to School Books

With his zest for adventure and confidence in trying new things, Woolbur is a delightful character! Follow along with Woolbur and his parents as together they navigate the emotions surrounding the first day of school. My favorite thing about this book is the author’s inclusion of first-day jitters for Woolbur’s parents. As moms we only want good things for our children while they are away at school, and the author is sensitive to that fear many of us may have about how our child will be perceived by others.

Take action: Share your feelings about the first day of school with your child. Be honest, but positive.

School isn’t so sure about all the new things he is experiencing on the first day of classes. He feels many common emotions that kids may experience as they navigate the transition to a new school year, which makes this a great talking tool. I particularly like how the janitor helps school prepare by explaining to him some of the things that are going to happen. In the end, School decides that maybe having children come visit isn’t so bad after all since he gets to make friends and learn lots of new things. This unique story is wonderful for older children who have lots of anxiety about going to school and need a little extra encouragement.

Take action: Ask your child what they are most looking forward to about school and what they may be nervous about. Problem-solve ways they can cope with these feelings.

This may not seem like the typical back-to-school book, but I love the message of community and kindness that this book emulates. It is a great talking tool for showing kids that they have agency over their words and actions and that what they do makes an impact in the lives of others. School is the perfect place to practice showing kindness and building a positive and safe community for all.

Take action: Brainstorm ways your child can show kindness to others while at school.

Rosie is excited for school! She can’t wait to meet her teacher and classmates, but on the first day of school she has some last-minute reservations. This sweet story illustrates the “butterflies” feeling many of us get when we are nervous and will show your kiddo that a little bravery goes a long way to conquering our fears of new experiences.

Take action: Have your child choose a few things they feel comfortable sharing about themselves so they will be ready for introductions!

Join this cute gang of monsters as they prepare for a new school year! From packing their bags to learning their letters, these monsters show just how fun school really can be. I love the bright and silly illustrations and how the book shows what different subjects your child will learn. Another great option for inspiring confidence in even the most nervous little monsters.

Take action: Talk your child through what their school day may look like so they know what to expect.

This is one of our favorite books and is a great addition to your back-to-school reading list. When Murray feels overwhelmed by his worries, his sister helps him create his own worry box where he can store his anxieties. A great introduction to coping skills, I highly recommend this book for preschool and up.

Take action: Create your own worry box using our DIY tutorial. Talk about specific school related worries and put them in the box.

The popular Pout-Pout Fish is back in this school tale. When Mr. Fish attends his first day of school, he is overwhelmed by all the things he isn’t sure how to do and becomes discouraged that maybe school isn’t the right place for him. A gentle reminder that kids don’t need to know everything and it’s ok to make mistakes – because that’s what school is for!

Take action: Practice group problem-solving with your child so they are ready to ask for help at school when they need it!

As the only dog in his class, Bailey stands out from his classmates, but he still finds many ways to enjoy the school day and do lots of learning. I love that this is a process book because it shows what a school day might look like from beginning to end. This is particularly helpful for kids who like to plan ahead and find comfort in knowing what comes next.

Take action: Talk with your child about the steps of their school-day routine.

There isn’t a single book I won’t recommend by Kevin Henkes and I love his school-related books so much they appear on both our Preschool and Kindergarten book lists! Chrysanthemum is so excited about starting school until she meets some of her not-so-nice classmates. This is an encouraging story about standing your ground and being proud of who you are.

Take action: Talk with your child about the importance of inclusion and kindness. If you believe your child is ready, here is a great article on how to approach the topic of bullying.

A sweet story about a little pig who will stop at nothing to attend school so he can learn how to read. If Rufus can do it, so can your kiddo! A gentle reminder that school is for learning but there are so many other great things for kids to experience while there – like story time!

Take action: Ask your child what they think their favorite part about school will be.

Comical on the surface, this book gets to the heart of the matter – school is full of newness and can cause feelings of worry and fear in kids. There are so many great talking points in this book which is one of the reasons I recommend.. Eventually pigeon realizes that all the things about school that he is worried about can actually be solved by…well, going to school!

Take action: Share with your child about a time you were afraid of something new. Discuss how you handled the experience.

As the mom of a daughter and son, this book made me cry! Henry and Liza have spent all their days together until Liza begins school. What will they do apart from each other all day? A beautiful book about transition and a unique look at the family members who remain at home when an older sibling starts school.