It’s normal for children to have mixed emotions about starting school, whether it’s their first day at a new school or their first time ever attending school or being away from their parents. Both of my kids have experienced major separation anxiety when starting school, so I am definitely no stranger to teary dropoffs and struggles getting used to a new school. It’s hard on them and it’s hard on you too, as the parent. Two things that worked for me were volunteering in the classroom and reading books about going back to school. Here are some favorites that I’m sure you will enjoy!
Our Favorite Going Back to School Books
“The Kissing Hand for Chester Raccoon” by Audrey Penn
Best for: Easing separation anxiety in younger children
This classic story is about Chester Raccoon, who is nervous about starting school. His mother shares a special secret with him: a special kiss in the palm of his hand that he can take with him wherever he goes. This is my all-time favorite book for the first day of school, and one that my children and I often talk about, even years after needing it.
“I Love You All Day Long” by Francesca Rusackas
Best for: Easing separation anxiety in younger children
This gentle story follows a young little pig named Owen as he learns that his mother’s love is with him all day long, even when they are apart. It takes him through the various parts of a normal school day with the sweet reminder that his mom loves him throughout each activity and even mishaps. It’s a sweet and soothing book for children who might be anxious about being separated from their parents during the school day. I love this and consider it one of my favorites for back to school!
“How to Get Your Teacher Ready” by Jean Reagan
Best for: Fun preparation for school
Part of the “How To” series, this book flips the script and gives children the power to “get their teacher ready” for school. It’s a fun and engaging way to ease into the new school year with a sense of playfulness and humor.
“Llama Llama Misses Mama” by Anna Dewdney
Best for: Younger kids struggling with separation from mom
Llama Llama is nervous about leaving his mama on the first day of preschool. The story follows him as he learns that even though Mama isn’t with him at school, she’ll be there to pick him up at the end of the day. This book is a reassuring read for young children who might struggle with being away from their parents.
“Bye-Bye Time” by Elizabeth Verdick
Best for: Toddlers and preschoolers
Part of Elizabeth Verdick’s “Toddler Tools” series, this book offers simple, reassuring strategies for saying goodbye. It’s an excellent resource for younger children who may be experiencing separation anxiety for the first time as they start preschool. I wish I had found this when my oldest was starting preschool.
My Back to School Coloring Book by Sweet Sprouts Publishing
Best for: Toddlers through 1st Grade
This back-to-school coloring book walks a young child through what they can expect at school. It starts with the morning routine including brushing their teeth, eating a healthy breakfast, and getting dressed for school. Then it walks them through what it’ll be like to go to school, meet their teacher and their classmates, and what they can expect to do during their day at school. And I LOVE that it also explains that they’ll go back again the next school day.
This coloring book has big bold coloring lines and large images, but it’s still fun and age-appropriate for up to 1st grade. This is a wonderful, interactive way to help your child get ready to start school. Be sure to pair with non-toxic crayons.
“School’s First Day of School” by Adam Rex
Best for: Understanding what to expect
This is a unique story about the first day of school that is told from the perspective of the school building itself. The sweet thing is that the school is nervous about the first day too! This book helps children understand what happens at school and reassures them that everyone—even the school—might have some first-day jitters.
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“The Night Before Kindergarten” by Natasha Wing
Best for: Preparing for the first day of kindergarten
Written in the style of “The Night Before Christmas,” this book takes children through the preparations for the first day of kindergarten. It’s a comforting and familiar way to ease anxiety about starting kindergarten. A lot of kids (and parents) find the transition from preschool to kindergarten challenging, usually because the days are longer and there are higher academic expectations. I love this book for this reason!
“First Day Jitters” by Julie Danneberg
Best for: Starting a new grade or at a new school
The story follows Sarah, who is anxious about starting a new school. The twist at the end—where we find out Sarah is actually the teacher, not a student—helps children realize that even adults get nervous about new experiences. It’s a lighthearted way to show kids that first-day jitters are normal. Even for grownups!
“How Do Dinosaurs Go to School?” by Jane Yolen
Best for: Teaching school-appropriate behavior
If you like any of the “How Do Dinosaurs” books, you’ll love this one, too! This book shows dinosaurs in various school situations, demonstrating the right and wrong ways to behave in a school environment. It’s a great tool for teaching young children about good behavior in a somewhat silly and entertaining way.
“The Pigeon HAS to Go to School!” by Mo Willems
Best for: Kids who are reluctant to go to school
Pigeon, the beloved character, is back; this time, he’s not so sure about school. Pigeon’s worries and excuses will resonate with children who might feel the same way. This book is perfect for making the idea of school less intimidating.
“Pete the Cat: Rocking in My School Shoes” by James Dean and Eric Litwin
Best for: Making school cool and relatable
Pete the Cat is cool, calm, and collected—even on his first day of school. This book is full of catchy songs and positive messages about exploring new environments, making it a great read for kids who might be nervous about school. If you aren’t familiar with Pete the Cat books, they’re sweet, funny, and wholesome—with a dash of Pete’s cool rock ‘n’ roll style. Don’t judge the books by the TV show. I was totally unimpressed by the show but love the books.
“Amelia Bedelia’s First Day of School” by Herman Parish
Best for: Kids who need a laugh
Amelia Bedelia’s literal take on everything leads to some funny and confusing moments on her first day of school. This book is a lighthearted way to help children see the humor in new experiences and not take things too seriously. If you’re a fan of Amelia Bedelia, you’ll love her first day of school.
“Maisy Goes to Preschool” by Lucy Cousins
Best for: Preparing for preschool
This colorful and simple book follows Maisy as she experiences a typical day at preschool. It’s a perfect board book for introducing young children to the routines and activities of preschool in a way that is fun and equally comforting.
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Going back to school can be a mix of excitement and nerves for children. And mamas, too! These first-day-of-school books are the perfect tools to help your little ones navigate their feelings, understand what to expect, and confidently ease into the school year.
Whether your child is dealing with separation anxiety, nervous about starting a new grade, or simply needs to know what to expect, there’s a book on this list that can help make the transition smoother and more enjoyable. Shop the full post on Amazon for even more recommendations on my favorite books for the first day of school! Happy reading.
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