24 Starting School Picture Books

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.

24 Starting School Picture 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!” [picture book, ages 4 and up]

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. [picture book, ages 4 and up]

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 makes a new friend, he realizes that Kindergarten is going to be fun! [picture book, ages 4 and up]

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. [picture book, ages 4 and up]

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! [picture book, ages 4 and up]

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? [picture book, ages 4 and up]

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! [picture book, ages 4 and up]

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. [picture book, ages 4 and up]

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! [picture book, ages 4 and up]

1. The Kissing Hand by Audrey Penn

The sweetest story ever about the magic of kisses to help with separation anxiety! [picture book, ages 4 and up]

More Starting School Picture Books

May’s Brave Day by Lucy Morris

The thought of starting school for the first time gives May butterflies in her stomach. In the garden where she does her best thinking, she tries to release her anxiety by jumping, hopping, and running but it doesn’t work. She doesn’t want to go to school but she discovers that her teacher is very nice, her classroom is very inviting, and the girl next to her lets her share her red crayon. Slowly, the butterflies recede, and May can finally eat breakfast on her second day of school! [picture book, ages 3 and up]

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. [picture book, ages 4 and up]

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. [picture book, ages 4 and up]

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. [picture book, ages 3 and up]

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. [picture book, ages 4 and up]

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! [picture book, ages 4 and up]

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! [picture book, ages 4 and up]

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. [picture book, ages 3 and up]

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. [picture book, ages 3 and up]

Lily’s Cat Mask by Julie Fortenberry

Starting school also means trying new things. In this case, Lily has to save the cat mask that she wears everywhere for 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. [picture book, ages 4 and up]

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. This is a great message about resiliency and coping. [picture book, ages 4 and up]

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. [picture book, ages 3 and up]

100th Day of School Picture Book

Miss Mingo and the 100th Day of School by Jamie Harper

I love how this book models many different ways to celebrate the 100th day of school, as well as the different ways to explore 100 as a number. Perfect for kindergarten! Jamie Harper combines a narrative story with facts that make this a fun learning experience. [picture book, ages 4 and up]

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. [picture book, ages 5 and up]

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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

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My books:

 Amazon / Signed or Inscribed by Me

Amazon / Signed or Inscribed by Me

Food for the Future: Sustainable Farms Around the World

• ⭐ Starred review from School Library Journal!
• Junior Library Guild Gold selection
• Massachusetts Book Award Long List
• dPICTUS 100 Outstanding Picture Books of 2023
• Chicago Library’s Best of the Best
• 2023 INDIES Book of the Year Awards Finalist
• Green Earth Book Award Long List
• Nautilus Silver Winner, Nonfiction Children’s Picture Book
• Imagination Soup’s 35 Best Nonfiction Books of 2023 for Kids

 Amazon / Barefoot Books / Signed or Inscribed by Me

Amazon / Scholastic / Signed or Inscribed by Me