10 Must-Read Books to Ease the Back-to-School Jitters (Especially for Kindergarten & First Grade!)

Writerverse Journey
Jul 24
4 min read

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The first days of school — whether it’s kindergarten, first grade, or transferring to a new school — can feel like an emotional roller coaster for little ones and their parents. Between the jitters, excitement, and unfamiliar routines, books can be powerful tools to help children navigate change with confidence, compassion, and curiosity.

Whether your child is anxious about making friends or simply unsure about what to expect, these 10 picture books are designed to support emotional readiness while sparking important conversations + check the bonus tips at the end of this blog post!

🎒 Back-to-school season can be easier — and even magical — when you lead with love and stories. Start with these 10 picture books and watch their confidence grow!

📚 Here are 10 back-to-school books that every parent of a kindergartener or first grader should read:

10. The King of Kindergarten by Derrick Barnes, illustrated by Vanessa Brantley-Newton

Summary: A confident young boy gets ready for his first day of kindergarten, full of optimism and royal flair.

Why it helps: With uplifting language and vibrant illustrations, this book turns nervous energy into joyful anticipation and sets the tone for a positive school experience.

9. First Day Jitters by Julie Danneberg, illustrated by Judy Love

Summary: Sarah Jane is reluctant to go to her new school… until a twist ending reveals the unexpected truth.

Why it helps: This humorous classic shows kids that everyone — even adults — get nervous, and that’s completely normal.

8. All Are Welcome by Alexandra Penfold, illustrated by Suzanne Kaufman

Summary: A beautifully inclusive classroom where everyone belongs, no matter what they look like, where they’re from, or what they eat.

Why it helps: This is the book every parent wants their child to hear before starting school — it builds a foundation of kindness, empathy, and acceptance.

7. Wemberly Worried by Kevin Henkes

Summary: Wemberly worries about everything, especially the first day of school.

Why it helps: Kevin Henkes captures childhood anxiety with heart and humor, helping children feel seen and supported.

6. We Don’t Eat Our Classmates by Ryan T. Higgins

Summary: Penelope the dinosaur learns that making friends means not eating them.

Why it helps: This hilarious, quirky story opens the door to talking about boundaries, kindness, and how to start friendships — even after mistakes.

5. The Pigeon HAS to Go to School! by Mo Willems

Summary: Pigeon really doesn’t want to go to school, but he has to — and he’s got a list of hilarious concerns.

Why it helps: Kids will laugh at the Pigeon’s antics while connecting with his fears. It’s a perfect read-aloud that lightens the mood.

4. Rosie Goes to Preschool by Karen Katz

Summary: Rosie prepares for preschool with enthusiasm and curiosity, showcasing her classroom, routines, and friends.

Why it helps: Especially useful for children transitioning from preschool to kindergarten, this book gently eases fears by showing what school life looks like.

3. The Day You Begin by Jacqueline Woodson, illustrated by Rafael López

Summary: A poetic exploration of what it feels like to be different — and how courage helps us connect.

Why it helps: This book fosters empathy and self-worth in children who might feel out of place, making it especially impactful for kids starting a new school.

2. Butterflies on the First Day of School by Annie Silvestro, illustrated by Dream Chen

Summary: Rosie feels butterflies in her stomach on the first day — but they start to fly away as she meets new friends.

Why it helps: A gentle metaphor for nervousness, this story gives kids language to express feelings and reassurance that the "butterflies" eventually disappear.

1. Along Came Oliver by Kelle Lima

Summary: When Oliver arrives, everything changes — including friendships. This story explores jealousy, inclusion, and emotional regulation with warmth and humor.

Why it helps: Back to school often means meeting new classmates and navigating social shifts. Along Came Oliver helps children process complex feelings, understand the value of empathy, and practice healthy communication.

Available in multiple languages (English, Spanish, Portuguese, and French) and its companion activity book extends learning through fun and is also available in a free printable version for teachers and parents — making it a versatile back-to-school resource you can return to all year long!

💡 Bonus Tips for Parents of Kindergarteners & First Graders:

Create a consistent routine a week before school starts — including bedtime and wake-up times.
Visit the school beforehand (or do a virtual walk-through) to build familiarity.
Validate their feelings. “It’s okay to feel nervous. I feel that way sometimes too.”
Read together daily. Books are powerful conversation starters and emotional bridges.
Let them pack their bag (preferably the evening before going to school) with a favorite stuffed toy or comforting object — even if it stays in the backpack all day.