If you have a little one starting preschool soon, you may be nervous about how they’ll handle the transition. To help prepare your toddler for their first day of preschool, I recommend reading children’s books with them that give a fun and comforting look into what their time at school will be like.

Personally, I was a worried wreck about my firstborn starting school when he was 2 years old. He was pandemic toddler who had been stuck at home with mommy for several months prior to his first day of school. I was nervous that he’d miss me, not like his teacher, or have a hard time getting along with other toddlers. I was pregnant and without childcare or family nearby, and I knew that I’d need help caring for and stimulating our toddler when the baby was born. Preschool was the best option for us at that time, but it didn’t stop my motherly worries.

A couple months before his first day of school, I starting reading these children’s books, listed below, to my son about going to preschool hoping it would make the transition easier. After reading together, we’d chat about what he thought preschool would be like. To my satisfaction, he started getting really excited for preschool! I involved him in the process of picking out his lunchbox and backpack. We would drive by the school and talk about what we thought the kids and teachers were doing. We circled the first day of school on the family calendar on our fridge and talked about it every day… “Four more days until the first day of school!”

I’m delighted to report that my son’s first day of preschool was a success! There were no tears, and he actually waved goodbye to me like he was glad I was leaving! The second week of preschool was when we started having some struggles saying goodbye. I think he realized that preschool was his new normal and maybe was concerned about how often he’d be away from mom. But, he only whimpered a little bit, never sobbed, and his teacher told me that once he got inside and started playing with his friends that he never asked about mommy again. I was so proud of us for making this transition together, but it also felt bittersweet. My baby was growing and didn’t need mommy all the time!

Help your little one prepare for preschool with our favorite picture books, below.

4 Best Books to Prepare Your Child For Preschool:

1. Preschool Day Hooray!, by Linda Leopold Strauss

Of all the books listed here, Preschool Day Hooray! was my son’s favorite book when we were preparing for preschool. The story positively shares a typical day in preschool from drop-off to pick-up with fun, upbeat rhymes. The children in the book do story time, dance, make arts & crafts, play outside, and even see what it’s like when someone gets an ouchie. Our favorite part was the end of the book when mommy comes back!

2. The 12 Days of Preschool, by Jenna Lettice

The 12 Days of Preschool is a fun book to read (or sing!) because it goes along to the same tune as “The 12 Days of Christmas” song. The book counts all the fun experiences children get to do at preschool in their classroom and outside, like sharing toy trains, riding tricycles, story time, and nap time. The colorful and busy pictures are fun for children to browse, and our book even came with stickers!

3. Our Class is a Family, by Shannon Olsen

I wanted our son to know that he would be safe and loved at school just like he is at home, and Our Class is a Family is a great book for sharing this concept. The book explains that school is kids’ home away from home where they are respected and accepted just the way they are. The book encourages children to build a community and strengthen friendships at their school. I loved this book for preschool prep, because it helped our toddler not feel intimidated by the new teachers and students he’d be spending his days with.

4. The Kissing Hand, by Audrey Penn

This book, The Kissing Hand, is wonderful for families dealing with separation anxiety. The story follows a child raccoon, Chester, who is nervous about his first day of school. His mother raccoon shares a sweet family secret that helps calm his fears and gives him the confidence to be away from home. This book is filled with empathy and compassion for little ones worried about being away from mommy and daddy. You can use it for more than preschool – day care, camp, overnights with grandma, etc. !

What favorite picture books have you read with your child to help with the transition to preschool? Please share your recommendations with me in the comments below! I’d also love to connect with you on Instagram and TikTok!

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