The collection contains thirty-five verses, including eleven poems that feature Winnie-the-Pooh illustrations.

The book's collection of poems have recurring themes of childlike innocence and characteristics that numerous scholars have studied.

The cognitive psychologist George Miller has argued that the poem "In the Dark" was inspired by crib talk.

[1] Furthermore, "In the Dark" can be read as an endorsement of childhood "as a golden era where... innocence, unqualified parental love, [and] irresponsibility" are commonly occurring traits.

[2] Author Elena Goodwin postulates that "King Hilary and the Beggarman" characterizes the poem's titular character as "like a small child, [that] excitedly anticipates the various Christmas gifts that" he will receive.