Told from the perspective of a disoriented bear, lost in the city, I Am a Bear by Jean-François Dumont, is a sensitive and understanding picture book about a bear who lives on the street with cardboard and paper for a bed. After several startling experiences with people, the bear sleeps away the day, barely noticed by people, until one little girl regards him. She labels him a teddy bear and comes back to visit him, which brightens the bear’s days.
I Am a Bear explores themes of homelessness and kindness.
An Education in Books Blog 
Sounds like a sweet, non-threatening way in to conversation about homeless.