Helpful First Day of School Books for Kindergarten and Preschool

Helpful First Day of School Books for Kindergarten and Preschool

Your child’s first experiences at school can be exciting, scary, anxiety-provoking, or a mix of all of the above. The list of first day of school books below can help you introduce the idea of school to a young child.

Why Books Can Help With The First Day of School

Heading off to school for the very first time is an exciting but scary idea for most kids. Many may be leaving their parents for the first time. New schools mean new rules, new friends, and new worries.

I’ve always found that the easiest way to explain new situations to my own kids is through reading about them in books.

The books below help to tackle different ideas – missing mom, anxiety about meeting new people, or learning about what teachers do to get ready for school. These are the perfect stories for the first day of school.

Finding the Perfect First Day of School Book for Your Child

There are sections for the first day of preschool books and the first day of kindergarten books. These books have characters headed into those specific classes so your child can experience school through the eyes of a character like them.

You’ll also find general books for the first day of school that are not grade-specific. These books might help you address feelings and new experiences with your child.

For more School-related books and book lists, Click here.

First Day of Preschool Books 

pout pout fish

Author: Deborah Diesen

Illustrator: Dan Hanna

Year: 2018

Genre: Picture Books

Age: 2 – 5

More info: Part of the Pout-Pout Fish series

Mr. Fish can’t figure out where to go, he can’t figure out how to write and he can’t figure out how to draw. He doesn’t think he belongs or is smart enough so his frown comes out as he thinks he wouldn’t ever get it right.

Finally, his teacher comes out to find him and tells him he IS smart, he WILL get it, and he DOES belong.

This is an adorable first-day-of-school book for kids with performance anxiety. If your child is worried about starting preschool, this is a great story to read!

Find this book in: First Day of School Books / Best Books for 3-year-olds

llama llama misses mama

Author: Anna Dewdney

Illustrator: Anna Dewdney

Year: 2009

Genre: Picture Books

Age: 2 – 7

More info: Part of the Llama Llama series

It’s Llama Llama’s first day of preschool and he is overwhelmed with feelings. He is trying to get used to the new toys and new surroundings but he just misses his mama. Soon he learns that it’s OK to love mama and have fun at school too. This was recently turned into a Netflix book adaptation starring Jennifer Garner.

A solid introduction to preschool separation anxiety and how kids can deal with it.

Find this book in: Books About Feelings / Anna Dewdney Books / Books for 2-year-old / First Day of School Books

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Author: Lucy Cousins

Illustrator: Lucy Cousins

Year: 2010

Genre: Board Book

Age: 2 – 4

Maisy’s easy sentences, bright colors, and brevity make it perfect for younger kiddos to learn the concept of school. If you are looking for a first day of preschool book, this is a very sweet pick.

In my house, Maisy was a much-loved character. If your child is starting preschool at ages 2 or 3, this is the perfect book for you.

Find this book in: First Day of School Books / Best Books for 2-year-olds

wemberly worried

Author: Kevin Henkes

Illustrator: Kevin Henkes

Year: 2000

Genre: Picture Books

Age: 3 – 6

Wemberly worries all the time, but she is especially worried about school. This story tackles the difficult topic of children with anxiety.

This was particularly helpful for my oldest child who has some anxiety in day-to-day situations but a lot of anxiety in new situations. He could relate to Wemberly and her feelings which opened a nice discussion for us.

Find this book in: Best Books for 3-year-olds / First Day of School Books

First Day of School Books for Kindergarten

Miss Bindergarten and other alphabet books

Author: Joseph Slate

Illustrator: Ashley Wolff

Year: 1996

Genre: Picture Book

Age: 5 – 6

More info: Part of the Miss Bindergarten series

Using the letters of the alphabet, readers meet each kid in the class as they get ready for school. We also see Miss Bindergarten get ready for school by cleaning, organizing, and decorating her classroom.

If you are looking for first day of school books for kindergarten, this is a really cute choice.

Find this book in: Best Books for 5-year-olds / First Day of School Books / Alphabet Books

the king of kindergarten

Author: Derrick Barnes

Illustrator: Vanessa Brantley-Newton

Year: 2019

Genre: Picture Book

Age: 5 – 6

After his parents call him the King of Kindergarten, a young boy experiences his first day of school in his new “kingdom.”

Sharing, learning, and the joy of making new friends are all explored in his sweet tale. This adorable pick from first day of school books it so uplifting.

Find this book in: Best Books for 5-year-olds / First Day of School Books

the berenstain bears go to school by stan berenstain

The Berenstain Bears Go To School  by Stan Berenstain

The beloved Berenstain Bears are back at it and tackling a new issue as only they can. Sister Bear is off to school for the first time.

I like that this story tackles the bus ride too – that can be very nerve-racking for some children. The Berenstain Bears have been helping kids for YEARS and this first day of school book is no exception

More Books for The First Day of School 

We dont eat our classmates

Author: Ryan T. Higgins

Illustrator: Ryan T. Higgins

Year: 2018

Genre: Picture Book

Age: 3 – 6

More info: Part of the Penelope Rex series

This hysterical story is all about a young dinosaur who has trouble making friends because she can’t stop eating them! It’s silly and funny especially a goldfish take a bite out of her little dinosaur finger. A little taste of her own medicine helps her learn her lesson.

If you want a great laugh, this first day of school book should be your choice.

Find this book in: Best Books for 4-year-olds / First Day of School Books 

Schools First Day of School

Author: Adam Rex

Illustrator: Christian Robinson

Year: 2016

Genre: Picture Book

Age: 5 – 6

This clever tale is written about School as he witnesses children and teachers using his facilities for the very first time. He is a little nervous as some say they don’t want to be there, but he starts to learn what the children learn and laugh at the jokes they tell. 

I absolutely love this first day of school book and the lovely twist. It’s a great story to prompt a discussion about your child’s first day of school worries!

Find this book in: Best Books for 4-year-olds / First Day of School Books 

David Goes to school and other first day of school books


David Goes to School by David Shannon

Back with his antics, David shows all the things your little one should NOT do at school.

From cutting the lunch line, to not listening, this book is great for first timers to learn what the expectations are at school.

Try asking your little one if they know what David should be doing in each situation instead!

How do dinosaurs go to school and other first day of school books


How Do Dinosaurs Go to School by Jane Yolen

In true dinosaur fashion, this story teaches the rights and wrongs of good behavior at school. This is especially good for boys who are prone to acting up.

While Wemberly Worried was best for my oldest, this one was made for my youngest. 😉

The pigeon Has to go to school

Author: Mo Willems

Illustrator: Mo Willems

Year: 2019

Genre: Early Reader

Age: 3 – 6

More info: Part of the Pigeon series

The Pigeon is back at it again with this hilarious story about why Pigeon doesn’t want to go to school. He knows everything already, right? So why exactly does he have to go?

Particularly good for kids not wanted to go back to school, I love the way Mo Willems captures big feelings and turns them into funny situations. As always, this story will leave your child in giggles.

Find this book in: First Day of School Books / Best Books for 3-year-olds

the kissing hand

Author: Audrey Penn

Illustrator: Ruth E. Harper, Nancy M. Leak

Year: 1993

Genre: Picture Book

Age: 2 – 5

More info: New York Times Bestseller

Little Racoon is heading off to school for the first time but is worried that he won’t feel comfortable in his new surroundings. Mrs. Racoon teaches him about the kissing hand so that he can have a piece of home in his heart wherever he goes.

This is a must-read in my opinion. It’s great for introducing the feeling of seperation anxiety with children going off to school, to a grandparent’s house, or for daycare. I used a version of the kissing hand method with my little one when he went off to preschool and it really does work!

Find this book in: Best Books for 2-year-olds / First Day of School Books

First Day of School Books Featuring Beloved Characters

Perhaps all your little one needs is a book featuring their favorite character going off to school. If that sounds right, then check out one of these books below.

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