Whether your child is starting preschool or heading into middle school, the first day can bring a mix of excitement, nerves, and lots of questions for both of you. One of the easiest ways to help kids feel more confident is by reading together. Stories give them a chance to see new experiences before they live them, ask questions, and talk through big feelings in a low-pressure way. If your family is getting ready for back-to-school, these are some of our favorite books to help start those conversations.
Around here, we believe confidence comes from preparation, not perfection. Sometimes a simple bedtime story is all it takes to make tomorrow feel a little less overwhelming.
Back to School Books: 12 Books to Prepare for The First Day of School
Llama Llama Misses Mama | In My Heart | Corduroy Goes to School
Back to School Books for Preschool
If this is your child's first classroom experience, chances are you're preparing too. These books can help you start conversations about separation, routines, and big feelings before the first day arrives.
Llama Llama Misses Mama by Anna Dewdney (ages 2-4)
This picture book is great if you anticipate that your child will have some separation anxiety during those first few days of school. Little Llama is excited to start preschool, but when it’s time for his mama to leave, he isn’t excited anymore. Learn how Llama Llama’s friends and teachers help him realize he can have fun at school, even though he misses his mama, and they will hug again with open arms at the end of the day.
In My Heart by Jo Witek (ages 2-5)
In My Heart explores a full range of emotions that your child can (and likely will!) experience not only in school but in life! This book helps your child understand what these emotions may feel like and how to name them. Between making new friends and learning about classroom communities and dynamics, this book can be a great tool to help your little one be prepared to not only experience these emotions but talk about them too.
Corduroy Goes to School by B. G. Hennessy (ages 2-4)
The beloved bear Corduroy is starting school! This book is great for your little one starting preschool for the first time. You and your child can interact by lifting the flaps and exploring Corduroy’s classroom and routines.
Wherever You’ll Be | Breathe Like a Bear | The Invisible String
Back to School Books for Starting Kindergarten
Kindergarten is a big milestone for kids and parents. These stories help normalize first-day jitters while reminding children they're capable of handling something new.
Wherever You’ll Be by Ariella Prince Guttman (ages 3-5)
This book explores the day of a working mother and her child, a young girl, while they’re apart. Wherever You’ll Be is a great reminder that even when you’re apart, you can pause and think of each other throughout the day to remind you that you’re still connected, even apart and you might feel scared. This book can be a great to read aloud together as a way to even reconnect with each other after those first few days of school.
Breathe Like a Bear by Kira Willey (ages 2-6)
This book is a great way to practice mindfulness techniques together! It’s a collection of 30 easy and short breathing techniques that your little one can easily do anywhere when they’re feeling nervous, frustrated, extra silly, etc. when they have those back to school jitters. The techniques help them to learn to manage their breath, bodies, and emotions. Which can be really helpful when starting school.
The Invisible String by Patrice Karst (ages 3-7)
Starting kindergarten might be the first time your little one is away from home for a full day! The Invisible String is the perfect book to remind them that we are all connected through an invisible string that can reach anywhere. It reminds them that even though you may not be physically together, you’re never alone.
Try asking: "When do you think you'll miss me the most at school?"
The Crayons Go Back to School | The Day You Begin | What Should Danny Do? | Save Me a Seat
Back to School Books for Elementary School
As kids get older, worries often shift from leaving home to fitting in, making friends, and navigating new social situations.
The Crayons Go Back to School by Drew Daywalt (ages 4-8)
The Crayons Go Back to School is another installment in the beloved series! Each crayon is excited to go back to school and learn new things about their favorite subjects. This might be a good read if your kiddo doesn’t want to start school once again, because it can remind them of all of the fun they can have back at school. the crayons are most looking forward to their favorite time of day, art class! This book is great for the night before the first day of school when your kiddo is feeling those first-day jitters and excitement to see their friends, make some new friends, and start the year!
The Day You Begin by Jacqueline Woodson (ages 5-8)
If your kiddo is nervous about fitting in when heading back to school, The Day You Begin is an inspiring story about being brave anyway. This book shows us that there are many ways that we are all different from one another. But when we share our stories and show who we are, we can all connect even though we are not the same.
Ask: "What do you think makes you different from other kids?"
What Should Danny Do? School Day by Adir and Ganit Levy (ages 4-7)
This super fun interactive school story has you choose your own ending! With 8 different endings, your child can explore the power of making choices and seeing the consequences of each choice in an exciting and unique way! How will Danny’s day at school end? It’s up to you!
Save Me a Seat by Sarah Weeks and Gita Varadarajan (ages 8-11)
Save Me a Seat follows the story of two fifth graders who don’t believe that they have much in common. Watch as they become friends and work together to fight a common enemy: bullying. This book covers the sometimes difficult social dynamics that come with school and friendships. This book can be relevant to any upper-elementary kiddo. But especially for one who may be nervous about making new friends.
Ask: "What could you do if you saw someone sitting alone at lunch?"
American Born Chinese | Freak the Mighty
Back to School Books for Middle School and Beyond
By middle school, the conversations often become less about the classroom and more about identity, friendships, and belonging.
American Born Chinese by Gene Luen Yang (ages 12+)
This story is about navigating the journey of discovering your self-identity through the story of a teenage boy who is the only Chinese-American student at his school. While not every reader can relate to the specific story of the main character discovering himself through his Chinese cultural background, most of us can relate to feeling different and struggling to meet the expectations of our peers. This book also reminds us that people come from varying backgrounds and contexts. And everyone’s story is unique and special, even if we can’t relate to it.
Freak the Mighty by Rodman Philbrick (ages 10-12)
This story follows two unlikely friends who could not be more different from each other in many ways, but both feel like outsiders. Freak the Mighty explores themes of bullying, isolation, and friendship. And reminds us that people are not usually as they seem to others. It reminds us that it’s important to get to know a person, and from that, a beautiful connection can form.
Prepare your child for the first day of school with these engaging reads that explore the challenges and triumphs of this exciting journey.
You don't have to "fix" your child's back-to-school nerves. Sometimes helping them name what they're feeling is enough to make those feelings feel a little smaller. Every school year brings something new, whether it's preschool drop-off, kindergarten carline, middle school friendships, or simply adjusting to a new routine. Reading together won't answer every question, but it creates space for the conversations that matter most.
And remember you don't have to navigate this season alone. We're here to help you feel more confident every step of the way.
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