Best Children's Picture Books About Starting School

Reassuring Kids' Books About Preschool, Kindergarten, and First Grade

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Children's picture books can help to reassure young kids about starting school or going to a new school. The books on this list are targeted at young children who are starting daycare, preschool, or kindergarten. In addition, there are several books for children who are worried about starting first grade, and one is also perfect for Talk Like a Pirate Day in September.

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'I Am Too Absolutely Small for School'

Happy father and son reading book together in bed
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Young children worried about starting preschool or kindergarten will be reassured when you read them the picture book "I Am Too Absolutely Small for School" by Lauren Child. Lola is sure she is "too absolutely small for school," but Charlie, her older brother, humorously and patiently convinces her she's not. Charlie gives Lola all kinds of funny reasons that stretch the imagination as to why she needs to go to school. Child's mixed media artwork definitely adds to the fun. (Candlewick, 2004. ISBN: 9780763628871) 

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'First Grade Jitters'

Cover art of children's picture book First Grade Jitters

Despite the similarities in titles, "First Grade Jitters" is very different from "First Day Jitters" (see listing below). In this picture book, a boy named Aidan shares his fears about starting first grade and tells how his friends helped him to feel better about starting school. The 2010 illustrated edition of Robert Quackenbush's book has appealing artwork by Yan Nascimbene. (Harper, an imprint of HarperCollins, 1982, 2010. ISBN: 9780060776329) 

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'First Day Jitters'

Cover Art - First Day Jitters

"​First Day Jitters" is for the child who is worried about changing schools. The author is Julie Danneberg, and the colorful and comic illustrations in ink and watercolor are by Judy Love. It’s the first day of school, and Sarah Jane Hartwell does not want to go. She will be going to a new school, and she is scared. This is a funny book, with a surprise ending that will cause the reader to laugh out loud and then go back and read the entire story again. (Charlesbridge, 2000. ISBN: 158089061X)

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'A Pirate's Guide to First Grade'

A Pirate's Guide to First Grade - Book Cover

Kids from kindergarten to second grade will be delighted with "A Pirate's Guide to First Grade." What would it be like to attend the first day of first grade with a band of imaginary pirates? The narrator does just that in this picture book, and he talks like a pirate as he tells all about it. It's an amusing introduction to first-grade activities from a unique perspective. There's even a glossary of pirates' lingo at the end of the book, making it an excellent book to share on Talk Like a Pirate Day, September 19. (Feiwel and Friends, an imprint of Macmillan, 2010. ISBN: 9780312369286)  

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'The Kissing Hand'

Cover of The Kissing Hand by Audrey Penn
Tanglewood Press

Transitions, like starting school, can be worrying for young children. Audrey Penn's "The Kissing Hand" provides comfort and reassurance to children ages 3 to 8. Chester Raccoon is scared about starting kindergarten, so his mother tells him a family secret: the story of the kissing hand. Knowing her love will always be with him is a great comfort to Chester, and the story may provide similar comfort to your apprehensive little ones. (Tanglewood Press, 2006. ISBN: 9781933718002)

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'Chu's First Day of School'


Chu, the adorable little panda first introduced in "Chu's Day," is back in this entertaining picture book by Neil Gaiman, with illustrations by Adam Rex. The story will tickle the funny bones of children 2 to 6. It will also provide some reassurance to children apprehensive about starting school as they learn about and laugh at Chu's experiences on the first day. (Harper, an imprint of HarperCollins, 2014. ISBN: 9780062223975)

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'Little School'

Cover Art - Little School

"Little School" is an enjoyable picture book about 20 preschoolers and the fun they have during a busy day at their school. The story follows all 20 through their preparations for school, a day at Little School, and their return home. This book is perfect for the child who is starting preschool, nursery school, or daycare and wants to know exactly what to expect. The book was written and illustrated in watercolor, pencils, and ink by Beth Norling. Although the book is out of print, it's in many public library collections. (Kane/Miller, 2003. ISBN: 1929132425)

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'First Grade Stinks!'

First Grade Stinks! - Cover Art of Children's Picture Book
First Grade Stinks! by Mary Ann Rodman, with Illustrations by Betih Spiegel. Peachtree Publishers

Are you looking for a children's book that can make your child's transition from kindergarten to first grade a little easier? In her amusing picture book "First Grade Stinks!," author Mary Ann Rodman tells the story of Haley and her first day in first grade. With unexpected sympathy and explanations from her first-grade teacher about why so much is different from kindergarten, Haley stops thinking, "First grade stinks!" and begins to think, "First grade is great!" (Peachtree Publishers, 2006. ISBN: 9781561453771)

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'Sam and Gram and the First Day of School'

Sam and Gram and the First Day of School - Kids' Book Cover Art

"Sam and Gram and the First Day of School" was written by Dianne Blomberg, has engaging watercolor illustrations by George Ulrich, and was published by the American Psychological Association. The book was written specifically to help parents prepare children for kindergarten or first grade. In addition to the story about Sam and his experiences on the first day of school, there are two sections of information for parents. (Magination Press, 1999. ISBN: 1557985626)

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'The Bully Blockers Club'

Cover art of The Bully Blockers Club picture book for kids
Albert Whitman & Co.

In "The Bully Blockers Club," Lotty Raccoon's first day of school is unhappy because of Grant Grizzly, a bully. With the help of advice from her sister and brother, Lotty begins to look for ways to stop the bullying. Even after her parents and teacher get involved, the bullying continues. A chance remark by Lotty's little brother gives her an idea that changes everything for the better. (Albert Whitman and Company, 2004. ISBN: 9780807509197)

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'Pete the Cat: Rocking in My School Shoes'

Cover art for Pete the Cat: Rocking in My School Shoes

Pete the Cat has four bright red high-top shoes, a backpack, a lunch box and a red guitar. The laid-back, groovy blue cat is ready for school, and nothing bothers him: not his first trip to somewhere new (the school library), not the loud and busy lunchroom, not the playground overrun with children, and not all of the different classroom activities. "Does Pete worry? Goodness no!" In fact, Pete just goes along singing his song and calmly accepting whatever happens.

"Pete the Cat: Rocking in My School Shoes" is a good book for kids 4 and up who need some reassurance about coping with school life. You can download the free companion Pete the Cat song from the publisher's website. For more about Pete the Cat, see a review of ​"Pete the Cat and His Four Groovy Buttons.​"(HarperCollins, 2011. ISBN: 9780061910241)

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'Wow! School!'

Wow! School! cover of picture book
Hyperion Books

If you are looking for a reassuring book about starting school (preschool or kindergarten) that will give you lots to talk about with your child, check out "Wow! School!" by Robert Neubecker. This almost wordless picture book features big, bright illustrations. It's Izzy's first day of school, and there's so much for the little red-haired girl to see and do. Each of the book's double-page spreads has a Wow! caption and a very detailed colorful and childlike illustration of some aspect of classroom and school activities.

The first spread, "Wow! Classroom" shows the entire room, including all the centers and bulletin boards, as well as the children playing and the teacher welcoming Izzy. Other illustrations include: "Wow! Teacher!," "Wow! Art!," "Wow! Books!," "Wow! Lunch!," "Wow! Playground!," and "Wow! Music!" This is a positive book and gives such a detailed look at what to expect that it should be a big hit with children ages 3 to 6. (Disney, Hyperion Books, 2007, 2011 Paperback. ISBN: 9781423138549)

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'Garmann's Summer'

Cover art of children's picture book Garmann's Summer by Stian Hole
Garmann's Summer by Stian Hole. Eerdmans Books for Young Readers

"Garmann's Summer" is unlike the many books about starting school that provide information and reassurance. Instead, this picture book focuses on six-year-old Garmann's fears about starting school and what he learns about life, death, and fear from his parents and his elderly aunts.  By the end of summer, Garmann is still scared about school, but he has come to realize that everyone has things that frighten them. 

"Garmann's Summer" was written and illustrated by Stian Hole and originally published in Norway. The mixed media collages are unusual and sometimes unsettling, effectively reflecting Garmann's feelings.  This book will resonate with certain 5- to 7-year-olds. (Eerdmans Books for Young Readers, 2008. ISBN: 9780802853394)

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'When You Go to Kindergarten'

Many children find comfort in routine. This picture book is filled with color photographs of active children in kindergarten classrooms. Rather than showing one classroom or just a few activities, the book shows a wide range of kindergarten activities in a variety of settings.

The book was written by James Howe and illustrated by Betsy Imershein. You and your child will enjoy talking about the photographs together. (HarperCollins, updated 1995. ISBN: 9780688143879)

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'The Berenstain Bears Go to School'

Brother Bear is looking forward to returning to school, but Sister Bear is fearful about starting school. She and her mother visit her classroom and meet her teacher before school starts, which helps. On the first day of school, Sister Bear is delighted to see friends on the school bus, but she is still worried. At school, she is a little scared at first but enjoys painting, playing, and stories. By day's end, she is glad to be in kindergarten. (Publisher: Random House, 1978. ISBN: 0394837363)