21 Must Read First Day of School Books

This was one of the first picture books we read together before Freddie started school, and it really stuck with us.

The idea of leaving a “kissing hand” for reassurance became part of our morning routine for a while.

It's quiet, sweet, and still one of my favorite ways to ease that first day of school anxiety.

Freddie thought the ending of this one was hilarious, and it actually helped him open up about his own nerves.

We read it the night before school started and ended up talking about all the little things that made him feel worried. It's a great mix of humor and comfort.

This book made us both laugh. The Pigeon has a million dramatic reasons not to go to school, and they all sounded pretty familiar at the time.

If your child is feeling reluctant, this one lets them feel seen without being too serious.

Freddie was really interested in this one. The idea that the school building could have feelings gave us a totally different way to talk about the first day.

It's thoughtful, funny, and just a little unexpected, which made it more engaging than I expected.

Related: First day of school crown

We didn’t read this until after Freddie had started school, but he loved spotting the different animals and hearing the rhymes.

It’s ideal for younger kids, especially if they’re heading into their first classroom experience. The tone is upbeat and the pictures are full of fun details.

Freddie got such a kick out of David’s antics. It led to some good conversations about rules without turning into a lecture.

This one’s great if your child is a bit of a rule-tester, or just enjoys a story with some chaos and humor.

Freddie went through a phase where he worried about everything, and this book helped him feel less alone in that.

Wemberly is such a relatable character, and the story shows that it’s okay to feel anxious but also okay to let go a little. It’s one I still recommend to parents dealing with big emotions.

We read this one more for fun than reassurance, but Chu’s giant sneeze got a laugh every time.

It’s short, silly, and easy to enjoy, especially with younger kids who might be a little nervous but not overwhelmed. It also helped break the tension on a morning when Freddie wasn’t in the mood to talk.

Related: First day of school scavenger hunt.

This one surprised us. Freddie was curious about how the animals felt when their friend went to school, and it turned into a nice way to talk about growing up and routines changing.

The gentle tone makes it a good pick for kids who are feeling a bit unsure about leaving home for the first time.

Pete’s songs were a big hit in our house, and this book had us singing along before we even opened the front door.

Freddie loved how chill Pete was about everything. It’s fun, rhythmic, and a great choice for making the morning feel upbeat instead of tense.

Clifford books were a go-to when Freddie was younger, and this one was no exception.

The story is simple and playful, and it gave us a way to talk about what to expect on that first day without making it feel like a big deal. It’s a great comfort read.

We had a whole stack of these dinosaur books, but this one got pulled out every August.

The silly situations made Freddie laugh, and it turned the idea of school rules into something approachable. A solid pick for kids who need a little humor to warm up to new routines.

This one hit me more than it hit Freddie at first. He wasn’t always great at expressing when he missed me, but this book helped him open up in small ways.

The story is gentle and warm, and it’s perfect if your child is working through separation anxiety in those early weeks.

Froggy’s chaos felt a little too familiar. Freddie loved that Froggy made mistakes and still had a good day in the end. It’s silly and relatable, especially for kids who feel a bit clumsy or unsure about routines. This one helped us laugh through a few rough starts.

This one’s a bit quirkier. Freddie liked how over-the-top the main character’s imagination was, and it gave him permission to be a little goofy too.

It’s not the most emotional story on the list, but it worked for us when the mood needed to stay light and playful.

We were already big fans of this series, so reading this before school felt familiar and fun.

It’s great for younger kids who already know the characters and need something cheerful. The chain-reaction silliness always led to questions and giggles at our breakfast table.

I remember reading this to Freddie the night before one of his first days, and he immediately got the “butterflies” part.

The metaphor made it easier for him to talk about how his body felt when he was nervous. It’s sweet without being too serious, which made it a quiet favorite.

This one became an instant hit in our house. The idea of a dinosaur trying not to eat her classmates was exactly the kind of humor that landed with Freddie.

It also sparked a few great chats about friendship and impulse control, without ever feeling like a lesson.

This story felt important. Freddie had a classmate with a name that others struggled to pronounce, and reading this helped him see how that might feel from the other side.

It led to a meaningful conversation about kindness and respect, and it’s one I think every child should read.

Molly Lou Melon was one of Freddie’s early favorites. He loved how confident and quirky she was, and I appreciated how the book encouraged self-acceptance without being preachy.

It’s great for building up a little bravery before walking into a new classroom.

This one made us both laugh. Freddie thought it was wild that the principal wanted school every single day, even weekends. It’s a good reminder that balance matters and that sometimes grown-ups get a little carried away too.

A nice one for setting the tone that school can be fun, but doesn’t need to be everything.