The Junie B. Jones series by Barbara Park begins on the evening of her very first Kindegarten orientation (where she meets her teacher "Mrs. who has another name but I just like to call her Mrs.") and follows Juniper Beatrice Jones through her early elementary education. The books are unique among early chapter books as they are as much fun for an adult to read as they are for your preschooler/early reader to listen to. Park's first person narrative takes us right into the mind of a smart, funny, curious kindergartner, with all the unfiltered, misheard, misspoken mishaps that lie therein.
I will warn you: Junie B. is not the squeaky-clean heroine of some other popular children's series. She tells little lies, does things she's not supposed to do, calls other kids names, and even uses the h word as in the nickname of one of her classmates, "That Jim I hate". That must be what's landed her on the list of Most Challenged Books year after year. But don't worry. Deep down Junie B. is a good kid who just gets sort of mixed up sometimes, like the time she lost one of her shoes in the bounce house at the school carnival and was worried because she needed both Pat and Leather, that's why.
The early books are especially good for getting your child ready for that first day of school. As they listen to Park's tales of Junie B. feeling fluttery inside, or her eyes getting a little bit wet, or being afraid to ride the bus the first day until she meets "that Grace" who becomes one of her two bestest friends in the whole world, they will feel reassured that kindergarten is a fun and exciting place where they will meet new friends, learn new things, and maybe even win a fruitcake at the school carnival.
Looking for more relatable books about school? Try the My Weird School series by Dan Gutman or the Diary of a Wimpy Kid books by Jeff Kinney. They will have your child laughing and counting the days until the first day of school. Or at least laughing.