This research paper provides four picture book suggestions that educators can bring into their classrooms to discuss the issue of homelessness. By analyzing both the text and illustrations of the books, it provides many suggestions on the stereotypes that exist within some of the books and the deconstruction of stereotypes in others. The hope is that this research paper will allow teachers to feel more comfortable bringing content on the topic of homelessness into their classrooms and play a role in helping students become aware of their own biases and pre-conceived notions.