Best First Day of School Books for Preschoolers

Penelope Rex is nervous for her first day of school. She wants to fit in, but all she can do is stand out as a dinosaur in a classroom full of children. As Penelope Rex learns how to make friends, your child will learn how to imagine what it feels like to stand inside someone else’s shoes (instead of eating them, even though they might be delicious). We Don’t Eat Our Classmates is a great Early Childhood Education tool to teach children about positive peer interaction, empathy, and friendship.Sarah, Percy and Bill wake in the middle of the night to find their mom has flown away. But these brave, wide-eyed owl babies know she will come home very soon. And of course, she does. Owl Babies is sweet, short, and easy for your preschooler to relate to. This book is particularly helpful during transitions, time away, or when introducing nannies or babysitters to your routine.Pete the Cat engages preschoolers and helps make ordinary moments fun. Pete the Cat keeps on “rocking in his school shoes” throughout his school day filled with playtime and learning. We find that this book is especially helpful when little ones don’t want to put on their shoes! The sing-along version (available on YouTube) is great for car rides or at-home dance parties.These three picture books are about saying goodbye, and the love of a parent or guardian that follows their preschooler wherever they go.

  1. In The Kissing Hand, Chester Racoon does not want to go to school; he wants to stay home and play with his mother like he is used to doing. But his mother’s special kiss sticks to his kissing hand all night long, and with her love he knows he will still have fun even though he is away from her. Chester Racoon decides to go to school, and he gives his mother a kissing hand too. There are Kissing Hand stickers in the back of the book, making this story an awesome parenting technique during goodbyes and transitions.
  2. Oh My Baby, Little One is about Baby Bird who misses his mother when he is away at preschool. His mother’s love follows him all day long, keeping them close until they are together again.
  3. I Love You All Day Long begins with a question, “Do I have to go today, Mommy?” Mommy Pig tells Baby Pig she loves him whether they are together or they are apart. I Love You All Day Long will help your preschooler feel their parents love throughout their busy day.

The Pout Pout Fish and Otter Goes to School are particularly helpful for children who are entering kindergarten or starting preschool. They will teach your child to believe in themselves and learn new things with confidence in their new environment.

  1. The Pout Pout Fish is a story about Mr. Fish’s first day at S.S. Rock Bottom Elementary. As he tries to find his way, he walks into all of the wrong classrooms; the fish seem so much bigger than him, and smarter too. He feels like he doesn’t belong, and he quickly decides that he wants to quit. On his way out the door, he hears an encouraging voice: his teacher, Miss Hewitt! In the brand-new fish classroom, Mr. Fish learns that “you don’t have to know things you haven’t learned yet!”
  2. Otter Goes to School turns schooltime into playtime. Otter plays teacher all day long, and though he tries his best, one of his stuffed students doesn’t understand his lessons. Otter worries that he isn’t a good teacher, until he finds a picture his student has drawn. Otter understands he is a good teacher after all!

We placed these stories together on our list because they will give your child memorable advice about how to be nice and respectful in his new classroom.

  1. How do Dinosaurs Go to School? will help your child understand proper classroom behavior while also proving that school can be a fun, playful and exciting new adventure. These fun question answer phrases will help your preschooler to understand that their behavior makes a difference for those around them.
  2. If You Ever Want to Bring an Alligator to School, DON’T! is about a little girl who thinks that bringing an alligator to show-and-tell is a great idea. As her show-and-tell dinosaur gets Magnolia into loads of trouble, she tries to assure the teacher that she has everything all under control. Along the way, she learns an important lesson about listening to grown-ups. These stories are both silly and serious, and your child will laugh and learn along the way.

These short and sweet picture books will provide your preschooler with a variety of ways to self-soothe and ask for help from others when they are experiencing negative emotions connected with separation anxiety. These four books can work in conjunction to help your children regulate their emotions when they are missing their parent or guardian while away at school.

  1. You Go Away is a short and simple picture book that will become a favorite for helping children understand their feelings when loved ones come and go.
  2. Bye-Bye Time is particularly helpful when a child is learning to self-soothe.
  3. When I Miss You is a part of a larger series called The Way I Feel: Taking Care of Our Emotions! This series helps a child to identify and handle their feelings with reassuring and simple language.

These picture books are designed to help children prepare for their first day of Preschool.

  1. The Night Before Preschool will help your child understand that everyone feels nervous before their first day at a new school, but before long the classroom will become a place for friends and fun.
  2. Maisy Goes to Preschool and Amanda’s First Day of School focus on making new friends and peer-interaction. We placed these stories together because they illustrate the day-to-day life of a preschooler as they make friends and learn new things along the way.

Llama Llama Misses Mama is a charming story about Llama Llama’s first day of school. This story’s simple language, illustrations and themes are easy for any child to relate to. Your preschooler will learn that it is okay to miss their Mama, and still have fun with their friends while they are away. Llama Llama Misses Mama will give your preschooler the resources to deal with emotions associated with separation anxiety in positive ways.I Like School is a wonderful book that is reader friendly for preschoolers and focuses on learning various objects in school. This is a great book to read before the first day of school so the children will be introduced to many school activities and encourage them to not be afraid of a different environment.How Rocket Learned to Read will show your child that it is fun to read the letters of the alphabet. This large picture book allows them to use their imagination and listen to intriguing stories which furthers their learning and engagement.Usborne First Experiences Going to School walks your child through a day at school so they will feel more comfortable when school is introduced on their first day. The short story is filled with pictures and uses simply, straight forward language that is easy for children to comprehend while leaving them feeling at ease.Smartypants (Pete in School) is a humorous book that describes how smart Pete, the dog, becomes after he eats multiple items including an encyclopedia. Your children will learn lessons of life and that school is filled with something new everyday.Charlie, the skilled and always hungry dog, walks you through a day in the life on the ranch and decides to share school with his animal friends so they can learn too. Your child will love to follow along to the painted pictures and laugh at the humorous language that is very relatable and reassuring to littles ones.

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