This sweet story is perfect for little ones who may be feeling anxious about leaving their parents to attend school for the first time. Chester and his mom create a comforting ritual that reminds them both that even while apart they can still feel each other’s love.

Take action: Create a “secret handshake” that you and your child can do before school drop-off as a comforting routine.

Wemberly worries – a lot. If your child is anxiety-prone this is a wonderful book filled with acceptance and encouragement. An honest story about managing anxiety, this book is sure to help your child see that being nervous about school is normal but that school holds many exciting new things that they needn’t be afraid of!

Take action: Talk with your child about their school-related worries. Share with them some of the fun things they can look forward to.

Once the excitement of drop-off dies down on the first day of school, many kids realize just how much they miss their parent! Follow along with Llama Llama as he overcomes separation anxiety.

Take Action: Help your child prepare for drop-off by practicing at home and talking about the different activities and things they may do in their classroom.

I don’t think I could love this book more! My daughter has what some may call a strong personality – she is confident and directive and sometimes struggles to make friends or follow rules because of this. This is the perfect book to help prepare strong-willed kids for the fun (and boundaries) that await them at school. We think you will fall in love with Penelope in this sweet story about connecting with others.

Take action: Practice introductions with your child so they are ready to make new friends with classmates who may be different than them.

Who doesn’t love the antics of the world’s most curious monkey? Join George as he visits school for the first time. We read this book almost every night when my daughter first started preschool. It was a great way to connect what she was experiencing with a well-known character.

Take action: After reading each page, point out objects and activities that your little may have in their own classroom. This helps them prepare for exploring at school!

Owen the mouse fiercely loves his trusty yellow blanket. When his parents try to help him break the attachment in time for the start of school, Owen wants nothing to do with it. Finally, a compromise is reached and everyone is happy. This is a great for kids who still use a security object and for parents who are gently encouraging them to let go.

Take action: Talk with your child about what they love most about home. Reassure them that those things (or people!) will still be waiting when they get back!

Join Mouse as he looks for his school supplies before the first day of school but ends up doing everything else instead! I just love how realistic this book is – anyone with a preschooler knows how distractible they can be when completing a task 😉

Take action: Have your child help pack their bag for the first day of school. Practice fastening, hanging, and taking it on and off.

A gentle story about inclusion and understanding, I absolutely love this book. Starting school means your child’s circle is expanding, and they will begin to meet many new people. Our hope as parents is that our child will always include and be included, but that isn’t always reality. This book reminds us all how important acts of kindness and making connections are for all people.

Take action: Talk with your child about what makes them feel loved and how they can show kindness and respect to others.

I really love that this book touches on some of the more abstract parts of going to school. There are so many great talking points to start a conversation with your little one about the importance of community. This book is sure to build your child’s confidence that at preschool they will feel welcomed, safe, and loved!

Take action: Using the illustrations in the book, identify with your child differences and similarities of the children pictured. Remind them that everyone plays a part in making the classroom a happy and supportive place.

Perfect for easing first day of school fears, this is a lovely little book. It accurately portrays the nervous excitement your little may be feeling before their very first day of preschool!

Take action: Walk your child through the fun activities they may be doing during the school day to generate some excitement!