Our Favorite First Day of School Books

It’s back-to-school season! Whether you’ve got a preschooler preparing for his first school experience or a rising fifth grader who is seasoned and suave, whether your children are starting the school year in person, with distance learning, or attempting homeschooling, reading picture books about the first day of school can help children of any age transition to the next stage or grade. Below, I’ve got you covered for whatever grade your children are starting! You can find books perfect for first-time preschoolers, kindergarteners, bus riders, elementary students… I’ve even got a few books perfect for the siblings being left behind when their older brothers or sisters start school! Be sure to scroll all the way down for the list(s) that might be best for your family.

And be sure to check out my list of our favorite school stories, stories that set children up for kind and confident school experiences! My friend Courtney from OT OuTside also has some incredible tips for helping children transition from summer to school on her website.

First Day of School Books Perfect for Preschoolers

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Please note that the first three books below aren’t explicitly written about preschool so could be read for entering kindergarten too… I simply felt that the classrooms and school routines described are more representative of a preschool experience.

• Wemberly Worried by Kevin Henkes — Though Henkes has written a few different books about school experiences (such as Chrysanthemum featured below), this one is perfect for all of the worries a child might have about that first preschool experience. Wemberly is a mouse who worries about just about anything and everything, and these worries amplify as she approaches the beginning of preschool. Henkes doesn’t give any specific strategies for dealing with these worries, but depicts them gently and empathetically, and this almost ambiguity is what makes Wemberly universally appealing.
• Ming Goes to School by Deirdre Sullivan, illustrated by Maja Löfdahl — This story, told with simple text and soft watercolors, walks young readers through a whole first year of school and all of the activities to be done and skills to be learned. We see the seasons pass and watch Ming accomplish new things, but one activity takes her almost the whole school year to try. Sullivan and Löfdahl provide a nice overview of a year in preschool as well as the important reminder (especially for parents) that learning something new sometimes takes time.
• The Kissing Hand by Audrey Penn, illustrated by Ruth E. Harper and Nancy M. Leak — A wonderful book for any child worried about leaving his mother and how she reassures him. Though this book is written about school, it’s sweet reassurance is perfect for any time of separation, such as travels, camps, or even babysitters. If you’re not able to find The Kissing Hand or simply need an alternative because you’ve read this one over and over again, give The Invisible String (you can read my review here) or Take a Kiss to School (see the kindergarten list below for more info about this one) a try.
• Rosie Goes to Preschool by Karen Katz — Done in Katz’s typical brightly colored collage, this book shows us preschool through Rosie’s eyes. In addition to the text, where Rosie tells us all about a typical day at preschool, Katz includes a small “Rosie Tip” on many pages, where Rosie gives preschoolers advice on how to navigate various situations that might come up at school, such as if they don’t get the jobs they wanted or if it’s ok to play by themselves. It’s those tips that make this a stand-out first day of preschool book.

First Day of School Books Perfect for Kindergarteners

Fortunately, there are TONS of books written specifically for rising kindergarteners, so they are easy to come by. After reading many, many of them last summer before my oldest entered kindergarten, and adding a few more new releases this year, we managed to narrow our list of favorite kindergarten-specific books down to the following. Enjoy!

• Mae’s First Day of School by Kate Berube — An endearing story about Mae and two new friends she makes as she climbs a tree to avoid her first day of school, Berube wrote and illustrated this one in a very accessible way. I love this one because all 3 characters are worried about very similar things, which boil down to “Will I have friends?”, “Will I know what I need to know?”, and “What if I miss my mom/dad/loved one?” Many children can relate to these three questions as they prepare to start school, and Berube addresses them explicitly yet gently.
• Monkey Not Ready for Kindergarten by Marc Brown — As you might be able to guess based on the title, the main character here really does not want to go to kindergarten. What makes this a winner to me is the way the parents help Monkey prepare for his first day of kindergarten— useful ideas for all parents out there!
• You’re Wearing THAT to School? by Lynn Plourde, illustrated by Sue Cornelison — Although the main character is indeed starting school for the first time, this story about being true to yourself could have teaching points for many young students, new to school or not. This would make a great companion text to A Bad Case of Stripes (see below) if you read that with older children. The author also includes a great page of “Tips for a Hippo Happy First Day of School” for students.
• Take a Kiss to School by Angela McAllister, illustrated by Sue Hellard — I love this one because it’s actually about the second day of school, not the first, making it perfect for those kids who are excited and enjoy the first day, but get nervous about going back once they see what it’s all about. This is also a great read for any families who have enjoyedThe Kissing Hand together.
• Chrysanthemum by Kevin Henkes — Henkes gives powerful messages about both being true to yourself and what makes you unique, as well as how to be kind and inclusive of people at school who are different than you. Henkes is a master of both school stories and stories that embody many near-universal childhood experiences, but Chrysanthemum may be my favorite from him!
• The King of Kindergarten by Derick Barnes, illustrated by Vanessa Brantley-Newton — A delightful new addition to diverse first day of school books, The King of Kindergarten is a nice partner to I Will Be Fierce (see my “First Day of School Books Perfect for All Ages” list below). The King enthusiastically approaches his first day of school as one might approach a new kingdom, holding his “head high and [greeting] everyone with a brilliant, beaming, majestic smile.” I love that these two books feature characters who approach the first day with confidence and enthusiasm, since many first day of school books are instead about overcoming fear and anxiety.
• Butterflies on the First Day of School by Annie Silvestro, illustrated by Dream Chen —  I love Silvestro’s literal take on the expression “butterflies in your stomach,” and I feel this book does a wonderful job of helping children understand what that means and find a way to verbalize the physical effects of nerves. As the main character, Rosie, moves through her first day, she realizes that her butterflies are slowly going away (by flying out of her mouth!). Rosie is also able to help another young student who is also butterflies in her stomach. This would be a great one to read if you suspect your own child has a case of the butterflies!

First Day of School Books Perfect for Bus Riders

For many of the youngest students (and their parents!), riding the bus to school can be one of the scariest parts of a new school year. Never fear, there are books for that, too! Check out these titles to help your little ones get comfortable with the school bus.

• School Bus by Donald Crews —  Crews writes phenomenal transportation and vehicle books for young audiences, and School Bus is no exception. Not written in story format, Crews simply teaches readers and listeners about school buses and what they do throughout the day.
• The Little School Bus by Margery Cuyler, illustrated by Bob Kolar —  Also part of a vehicles series, Cuyler and Kolar invite young bus riders to join a bus and its driver, Bob, as they journey throughout a day. Unlike School Bus, The Little School Bus is indeed written in story form (and rhymes), so some parents may prefer reading this one aloud.
• I’m Your Bus by Marilyn Singer, illustrated by Evan Polenghi — Another school bus story written in verse, I’m Your Bus is told as if the bus is talking to its newest passengers, teaching them all about herself and what they can expect from both their bus rides and their school days.

First Day of School Books Perfect for All Ages

To help your kiddos start their school years off on the right foot, consider reading some of these wonderful books that help set students up to be the best student, classmate, and friend that they can be in a new school year. In my opinion, these are worth purchasing for all home and school libraries!

• School’s First Day of School by Adam Rex, illustrated by Christian Robinson — In one of my favorite back to school books in any category for any age, Rex writes about first-day nerves from the school’s point of view. The school’s feelings about the day cover quite a spectrum as the day passes, and Rex somehow manages to develop the students’ characters deeply, though we’re only hearing the story as told by the school. Robinson’s illustrations are, as always, brightly colored, fun, and diverse!
• Truman by Jean Reidy, illustrated by Lucy Ruth Cummins — Similar to School’s First Day of School, this is a story about the first day of school told from a different perspective… That of Sarah’s pet turtle! Truman and Sarah have a sweet life together in a big city, playing, coloring, and watching the world go by. Until, one day, Sarah eats a special breakfast, puts on new clothes, straps on a big backpack, and tells Truman to be brave. This story is funny, endearing, and full of courage. It’s bound to bring smiles to all, especially those who may be a little unsure about starting school.
• All Are Welcome by Alexandra Penfold, illustrated by Suzanne Kaufman — This one is a perfect text for any teacher, any grade level, to share on the first day of school! Penfold and Kaufman link welcoming text and diverse illustrations to show both students and families that everyone is indeed welcome at this school. Wouldn’t it be wonderful if every classroom in every school started the year with this open-arms mentality? If you buy this for your classroom and are like me, quickly trashing dust covers, you’re going to want to save this one to display the diverse and welcoming poster hidden on the inside!
• A Bad Case of Stripes by David Shannon — Great for the first day at any grade level or for reading with children worried about fitting in any time during the school year, this is more text-heavy, so readers need slightly longer attention spans. That said, both of my girls (ages 6 and 3.5 at the time of writing this) love this story of a girl worried about what others will think of her when they discover that she likes lima beans. As she works hard to conform to what she believes is acceptable to her peers, the main character endures something surprising, and it’s only when she learns to be herself that she is cured.
• First Day Jitters by Julie Danneberg, illustrated by Judy Love — A cleverly written story about first-day nerves with a surprise twist in the end, this is a VERY popular book for teachers to read out loud on the first day of school. You could pair this with School’s First Day of School and Truman for wonderful conversations about perspective and experience!
• The Name Jar by Yangsook Choi — The Name Jar is wonderful for new students in school, especially as it relates to welcoming and accepting immigrants. Choi addresses themes of acceptance, being yourself, respecting differences, and making new friends. Followers also recommended Chocolate Milk, Por Favor if you’re looking for an additional title.
• I Will Be Fierce by Bea Birdsong, illustrated by Nidhi Chanani — Written by a former teacher, this new arrival (published in April 2019) is bound to make an impact this fall. Featuring a diverse multicultural cast, I Will Be Fierce equates the first day of school with a knight’s quest, in which the girl jumps out of school on the very first day exclaining, “Today, I will be fierce! I will answer the call to adventure.” She’ll inspire readers of all ages to approach school with tenacity, to make the most out of the experience, and to stand true to the kindness they know is right. See The King of Kindergarten above for another new book about walking into that first day of school with confidence.
• The Day You Begin by Jacqueline Woodson, illustrated by Rafael López — At one point or another, and for some children more often than not, we all feel like outsiders. As adults, we need to help our children understand these feelings and work through them, while also celebrating our individuality and unique characteristics that make us special. Just as importantly, we need to help raise our children’s awareness of when others may be feeling like outsiders. Reading books like The Day You Begin can help us to do all of the above.
• Your Name is a Song by Jamilah Thompkins-Bigelow, illustrated by Luisa Uribe — Okay, y’all, Your Name is a Song is an incredibly important book for both children and adults to read in the back-to-school season (even if back to school means back to distance learning!). It’s important for students and teachers who worry about how others will say their names on the first day of school and the families who support them. Important for teachers who studiously review their class lists to prepare for the first day of school. Important for students who yearn to create a welcoming environment for new students in their classes, and important for parents who help their children develop traits of inclusivity and respect. You can read my full review here. 

Poems About School

• A New School Year: Stories in Six Voices by Sally Derby, illustrated by Mika Song — An anthology of poems from the voices of 6 children, kindergarten through 5th grade, chronicling emotions and experiences from the night before school starts till the bell rings at the end of the first day, this unique take on a first day of school story will delight older readers. Given it’s format, younger children may enjoy reading this in “chapters” too, such as reading “The Night Before” in one sitting, or all the kindergarten stories in one sitting.
• Did You Hear What I Heard? Poems About School by Kay Winters, illustrated by Patrice Barton — Though these school poems encompass more than just the first day of school and are told from various perspectives, the collection of poems is a fun read for any school-aged children. I always love Barton’s illustrations, which here highlight diverse students and kind teachers interacting with each other.

Books Perfect for Younger Siblings Whose Older Brother or Sister are Starting School

• Maple and Willow Apart by Lori Nichols — Check out this testimonial that a dear friend guest posted for me last fall about the impact the whole Maple and Willow series has had on her children!
• Truman — Yes, Truman is on here twice. It’s such a good first-day-of-school story, but it’s also perfect for those who are being left behind by the loved one starting school!

Our Favorite Just-For-Fun Book About School

• If I Built a School by Chris Van Dusen —  No, this one’s not really a first day of school book… But I couldn’t resist adding it to my list! If you’re a Chris Van Dusen fan, then yes, this lives up to what you might except based on how wonderful his other books are. If you don’t know Chris Van Dusen, then you need to remedy that right now– start by reading my reviews of some of his books here, here, and here.

As far as first day of school books go, you may have noticed that I haven’t included many of the books in which popular characters have their first days of school (like The Pigeon HAS to Go to School, Maisy Goes to Preschool, and The Berenstain Bears Go to School). If your child has a favorite character (like Pete the Cat or Amelia Bedelia), that character’s series probably includes a first day of school book, and reading about a character to whom she is attached may be especially impactful for your child!

If you still need more, check out my list of our favorite stories about school. And, for those of you who have children who are especially worried or anxious about starting a new school year or a new school, be sure to check out my list of terrific books to help children process fear and worry!

What are your favorite first day of school books to read with your children?