Top 10: Starting School Books

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A reader asked me to help her round out her list of books for incoming Preschoolers. I searched, and there are not tons of them. I decided to combine this with entering Kindergarten because, in September, my youngest child will start Kindergarten. I feel that you can use the books somewhat interchangeably and that books that your child enjoys will be a more important factor than whether the book aligns exactly with his or her school entry point.

With regard to my youngest entering Kindergarten, I’m not that sad about that. I’m sadder that he is elongating and losing his baby chubbiness in his face and legs. I made the mistake with my middle child thinking that she’s been to elementary school so much as a tag-along that she’d have no anxiety or transition issues. But a transition to a new grade or school, no matter how small, is still difficult for children.  It’s helpful to visit the new school as often as possible.

Play with kids that will be at the same school if you can.  And read, read, read to your child books about starting school. The familiarity of routines and activities of the new school will take a lot of the anxiety away. So, while my youngest has been visiting his elementary school for 5 years so far, we’ll take it one step at a time and read these books over and over to ensure a smooth landing in September. And a few play dates with new friends is also on the books!

p.s. I also have a post on Getting Kids Ready for Kindergarten Activities with great advice from an Occupational Therapist and Has Kindergarten Changed or Are Kids Smarter from Harvard Education Letter.

Starting Kindergarten and Preschool Books

10. Mama Don’t Go by Rosemary Wells

Yoko has trouble separating from her mother during the first week of school, but her new friend Timothy helps her to understand that mothers “just keep coming back!”

9. Welcome to Kindergarten by Anne Rockwell

At first, everything seems so big and overwhelming, but after going over the routines of Kindergarten it feels just right to the little boy in the story.  A sweet and gentle depiction of the routines of Kindergarten.

8. Look Out Kindergarten, Here I Come by Nancy Carlson

Henry the mouse is so excited about starting kindergarten .. .that is, until he walks through the door to class.  But as he recognizes all the things he talked about and made a new friend, he realizes that Kindergarten is going to be fun!

7. My First Day at School by Ruth Wickens

My kids liked this book because it’s a pop-up book and it talks about the first day of preschool with a little boy learning about all the wonderful options of fun things to do at preschool as well as the routines.  My kids liked to read this book well into preschool just to compare what is the same and what is different about their preschool.

6. Miss Bindergarten Gets Ready for Kindergarten by Ashley Wolff

A glimpse of what the teacher does to get her classroom ready for the kids in her class!  It’s not all nicely set up and attractive to kids by accident!

5. Sumi’s First Day of School Ever by Soyung Pak

Sumi doesn’t speak English and today is her very first day of school ever.  Will it go well?

4. D.W.’s Guide to Preschool by Marc Brown

D.W. is an old-hand at preschool and is reassuring about how much fun it is!

3. Wemberly Worried by Kevin Henkes

Wemberly is a worrywart and she is especially worried about starting school.   It turns out that her teacher is really nice and encourages her to make a new friend who is very similar to Wemberly.

2. I Am Too Absolutely Small for School by Lauren Child

Lola thinks she is “too absolutely small for school” because she is a little nervous about starting school.  Or is it Soren Lorenson, her invisible friend, who is nervous?  But all is well when she makes a new friend on the first day.  Lola is her usual delightful and funny self!

1. The Kissing Hand by Audrey Penn

The sweetest story ever about the magic of kisses to help with separation anxiety!

More Starting School Picture Books

Norman’s First Day at Dino Day Care by Sean Julian

Is Norman an invisible dinosaur? No. He’s just shy (and tiny which makes it easy for him to hide). It’s his first day at dino daycare and it’s hard to jump in. But that’s ok. His teacher and new friends help him and he finds that he is courageous as well as shy.

Ollie and Augustus by Gabriel Evans

Ollie’s dog Augustus is huge and they do everything together. But now that Ollie is going to start school, what will Augustus do all day when he’s gone? Ollie decides to find a friend for Augustus but it doesn’t go well. When Ollie goes to school, he worries and worries. When he comes home, he finds that Augustus is just fine.

Play Day School Day by Toni Yuly

An older sister gently describes what school is like to her younger brother who will be going to school for the first time. As they play together, acting out the routines of school, nature serves as its own school. The two siblings have a lovely day playing together and they both look forward to starting school. This is a comforting way to think about starting school.

Mae’s First Day of School by Kate Berube

It’s Mae’s first day of school but she says, “I’m not going!” Her mother makes her go and on the way to school, Mae is sure that it’s not going to be fun. She ends up at school… up a tree. Rosie joins her. Rosie isn’t going to school either. A tall lady joins them on a tree branch. She’s Ms. Pearl. They eat cookies from Mae’s lunchbox and find out that they are all afraid of the same things. There is a great solution to this though and they find that together, they are ready to start. This is a cute first day of school story for anxious kids who like to climb trees.

Kindergarrten Bus by Mike Ornstein, illustrated by Kevin M. Barry

This is the perfect picture book for pirate lovers who are starting school and feel a little nervous about it. Mike Ornstein utilizes every pirate reference that I can think of to comic hilarity in this sweet story of a pirate bus driver, his charges, and his parrot. The illustrations further push the pirate theme, including an “Emergency Plank” and a personalized license plate. This is a fun starting school picture book for landlubbers too!

It’s Your First Day of School, Busy Bus! by Jody Jensen Shaffer, illustrated by Claire Messer

This is another spin of starting school anxiety and this time it’s the bus that is nervous because it’s the first day of school for the bus! The bus driver goes through thorough checks to make sure the bus is in perfect working condition, but the bus still worries. Will the kids have fun? Will the bus get homesick? Will the bus make friends? When it’s time to get the children, the bus realizes that he is safe, clean, and loved and he’s going to have a great school year! This would be a fun picture book for kids who are nervous about starting school and taking the school bus for the first time!

Is Your Buffalo Ready for Kindergarten? by Audrey Vernick, illustrated by Daniel Jennewein

Your buffalo is growing up. He plays with friends. He shares his toys. He’s smart! But is he ready for kindergarten? (And is kindergarten ready for him?)

Is Your Buffalo Ready for Kindergarten? is a hilarious look at first-day-of-school jitters from author Audrey Vernick and illustrator Daniel Jennewein.

Mom, It’s My First Day of Kindergarten! by Hyewon Yum

It’s a child’s first day of kindergarten, but who is worried about all the new people and the different things he’ll meet–the child? No! The mother. In a refreshing reversal of roles, the child takes it upon himself to comfort and reassure his mother that everything will be fine, she’ll get used to him going to big-kid school, and yes, he is ready for the first day of kindergarten. Utterly charming in its simplicity, Yum playfully uses size and color to reveal the emotions of this milestone beginning.

Lily’s Cat Mask by Julie Fortenberry

Starting school also means trying new things. In this case, Lily has to save her cat mask that she wears everywhere for just recess time when she starts school. The cat mask has become a crutch for Lily when she doesn’t want to talk or feels mean. Her teacher, Ms. Ito, realizes this. Making changes is hard, but Lily is able to do it and there’s even a costume party in her class where she can wear her cat mask and make a new friend.

When You Need Wings by Lita Judge

This could be the first day of preschool for a little girl who faces a scary transition at drop off by using her imagination to find her safe place. A great message about resiliency and coping.

Choo-Choo School by Amy Krouse Rosenthal, illustrated by Mike Yamada

This rhyming picture book of trains starting their first day of school mimics the routines that young ones will go through in their school day. Interestingly, the teacher at Choo-Choo School is human while the students are trains. The font is not my favorite but this is a good book for kids who love trains and are starting school for the first time.

100th Day of School Picture Book

Planet Kindergarten: 100 Days in Orbit by Sue Ganz-Schmitt, illustrated by Shane Prigmore

Celebrate the 100th day of kindergarten with this adventure-in-space picture book. In just 100 days of school, kindergarteners have learned so much! Use this book of space achievements to connect to what students have done in class.

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p.s. Related posts:

Multicultural Starting School Books for Kids

Getting Kids Ready for Kindergarten

New Back to School Picture Books

Starting Kindergarten Picture Book of the Day

Rising Kindergarten Summer Reading List

Kindergarten Readiness FREE Printable Book: My Book About Me

Picture Book for Parents with Kids Back in School

Top 10: Best Quirky Schools in Children’s Books

Connecting Reading with Writing in Kindergarten


My books:

BEST #OWNVOICES CHILDREN’S BOOKS: My Favorite Diversity Books for Kids Ages 1-12 is a book that I created to highlight books written by authors who share the same marginalized identity as the characters in their books.

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