Jacob’s New Dress by Sarah and Ian Hoffman
Plot Summary: Jacob loves playing dress-up, when he can be anything he wants to be. Some kids at school say he can't wear "girl" clothes, but Jacob wants to wear a dress to school. Can he convince his parents to let him wear what he wants? This heartwarming story speaks to the unique challenges faced by boys who don't identify with traditional gender roles.
Youtube link: https://www.youtube.com/watch?v=z3_5W2zDg6k
Jacob just really likes dresses even though his classmate Christopher is teasing him and telling him he can’t. Although it takes his parents a likely-realistic moment to wrap their heads around sewing a dress for him, Jacob is beyond excited about the purple dress. It's really a cross dressing story, not a trans story as Jacob feels like a boy, he just doesn’t understand why dresses are “girl clothes.” Kids get caught up in “boy things” and “girl things” sometimes and this is a good book to make them think why not a boy in a dress.