15 First-Day-of-School Books to Banish Jitters

The first day of school is a huge milestone for kids…but it’s not one that all tykes embrace with open arms. Beginning preschool or kindergarten can be a little scary. That’s where these first-day-of-school books come into play! These first-day-of-school books are designed to give little ones a sense of what to expect and ease their nerves (and calm Mom or Dad’s first-day jitters, too!).

For tots who are heading to school for the first time, we hope these first-day-of-school books get them excited for the year to come! 

The King of Kindergarten

Written by Derrick Barnes, illustrated by Vanessa Brantley-Newton

If you want to pump your little one up for the first day of school, there’s no better role model than the confident hero of this book! “The King of Kindergarten” takes on this big milestone with gusto—leaping into new experiences head-first and quickly winning over the rest of the “kingdom.” It’s a joyful look at the first day of school, whether your kiddo is starting kindergarten, like the titular king, or is still in pre-K or preschool.

Llama Llama Misses Mama

Written and illustrated by Anna Dewdney

Is your little one leaving Mom or Dad for the first time? This story about Llama Llama’s first day of preschool will totally resonate.  It’s a great way to address your tyke’s school worries and separation woes.

The Day You Begin

Written by Jacqueline Woodson, illustrated by Rafael López

For tots who are apprehensive about walking into a new school where they may feel different from their classmates this book is here to help them find courage.

First Night of Howlergarten

Written and illustrated by Benson Shum

This imaginative tale gives first-day-of-school nerves a hair-raising twist! Sophie isn’t entering kindergarten, she’s prepping for her first day of howlergarten—a special school for supernatural tykes.

Mr. S

Written by Monica Arnaldo

Bring a smile to your school-bound kiddo’s face with this silly mystery about the first day of school. When the students of room 2B arrive, there’s no teacher to be found, but there’s a sandwich on the desk and the words Mr. S scrawled on the blackboard. Hilarity ensues!

We Don’t Eat Our Classmates

Written and illustrated by Ryan T. Higgins

What happens when a hungry T-rex starts school…but her classmates are all tasty-looking humans? Kiddos find out in this laugh-out-loud tale! 

Butterflies on the First Day of School

Written by Annie Silvestro, illustrated by Dream Chen

It’s the first day of school, and Rosie has butterflies in her belly…and this imaginative tale takes that figure of speech literally! As Rosie warms up to the idea of school and makes new friends, the butterflies roiling in her tummy flit away one by one, leaving her feeling totally comfortable and confident by the end of the day.    

The Pigeon HAS to Go to School!

Written and illustrated by Mo Willems

Kids’ favorite back-talking bird is at it again! Now, it’s time for Pigeon to go to school—but he doesn’t want to…until he comes to realize that school is exactly where he wants to be. This story addresses apprehensions with silliness and sass.

School’s First Day of School

Written by Alex Ross, illustrated by Christian Robinson

This book flips the whole first-day-of-school-nerves theme on its head and presents the first-day experience through the eyes of…the school itself! For little ones who have never attended school before, it’s a nice introduction to all of a school’s fun features…from the story circle rug to the playground to the walls decked-out in student art. 

Miss Bindergarten Gets Ready for Kindergarten

Written by Joseph Slate, illustrated by Ashley Wolff

In this rollicking rhyming story Miss Bindergarten is gearing up for the first day of school, where she’ll meet her 26 new students. Oh, and each student’s name starts with a different letter of the alphabet, making it a fun way to prep for the school year and brush up on A-B-C’s. 

Lena’s Shoes Are Nervous: A First-Day-of-School Dilemma

Written by Keith Calabrese, illustrated by Juana Medina

Lena starts kindergarten today, and she’s picked out all her favorite clothes for the occasion…there’s just one little hiccup. Lena’s shoes are nervous! But by the end of the book, they remember how to be brave, so Lena and her shoes can have fabulous first day.

A Letter From Your Teacher: On the First Day of School

Written by Shannon Olsen, illustrated by Sandie Sonke

Written as a letter from a teacher, this book sets up school as a warm and welcoming environment. Knowing they’re in the capable hands of a caring teacher will boost your kiddo’s confidence and excitement as they venture into their own first day! 

William, The What-If Wonder on His First Day of School

Written by Carol Wulff, illustrated by Clare Willet

William, a new student, is anxious about his first day of school…until he discovers a new way of thinking that helps him banish his jitters and have an amazing day! His journey—penned by a child psychologist— teaches kids how to face their fears and look at going to school as a new adventure. 

On the First Day of Kindergarten

Written by Tish Rabe, illustrated by Laura Hughes

Saying “bye” to Mom and Dad can be hard, but this book focuses on all the fun experiences new kindergarteners get to say “hello” to! The many exciting firsts depicted within the pages of On the First Day of Kindergarten will surely give your kiddo lots to look forward to.

Stanley the Dog: The First Day of School

Written by Bobby Bones, illustrated by Stephanie Laberis

Even pups can be apprehensive about the first day of school—at least that’s the premise of this pooch-led tale. In this lighthearted story, it’s time for Stanley the dog to start school…but he’d rather stay in bed. But soon Stanley overcomes his worries, realizing that being himself is the best way to conquer the day! Stepping into unknown territory can be stressful, but Stanley’s there to show kids how to muster up the bravery it takes.

You May Also Be Interested In...

• How to Get Your Child Ready for Preschool or Kindergarten
• The Ultimate Baby & Toddler Book List
• Educational Apps for Toddlers and Preschoolers
• Dr. Harvey Karp's Tips For Calming Toddler Fears

Disclaimer: The information on our site is NOT medical advice for any specific person or condition. It is only meant as general information. If you have any medical questions and concerns about your child or yourself, please contact your health provider.