Winnie-the-Pooh relates the adventures of the favorite stuffed bear of the author's son. Written in the voice of the father-author, it addresses readers through the voice of a father inventing stories for his son.  The introduction presents Christopher Robin, the namesake of the author's son, the bear named Winnie-the-Pooh, formerly titled Edward Bear, and Piglet.  The bear's name change is a delightful part of the recounting. Following are ten chapters acquainting us with Rabbit and his endless relations, a forlorn donkey named Eeyore, a verbose Owl who knows his scholastic limitations, Kanga and Baby Roo, and a supporting cast comprised of bees and an unseen woozle and heffalump.

We are taken into a world of autonomous creatures living in a private wood, each with his own home and whimsical daily doings. Christopher Robin can solve any dilemma, however he does take cues from Pooh when a rescue of a flood bound Piglet is in order. Rather Christopher Robin is about his own business of being alive and pursuing what curiosities may stir him, and the animals follow their inclinations likewise. Decorations, or drawings, in the story were created by the Punch cartoonist and co-worker of the author, Ernest G. Shepard.

Chapter 1 brings us the young child pulling Winnie-the-Pooh behind as he descends the stairs to visit his father in the evening. The author speaks to the reader, telling us what Pooh may be thinking as he is dragged down the stairs. Then, in response to Christopher Robin's statement that Pooh wants a story about himself, the author begins. Chapter 1 relates a story of Pooh and his quest for honey, returning to the story time setting as the little boy heads back upstairs for a bath, dragging Pooh behind. Chapters 2 through 5 each are complete adventures, gradually introducing more characters, with no allusion to the author and the boy and bear at his side. At the end of Chapter 6 we are reminded a father is telling these stories to his son's bear, when the boy asks details about his birthday gift to Eeyore. At the end of Chapter 9 the author includes an aside to the reader. And Chapter 10 ends the same as Chapter 1, with the author describing Christopher Robin bumping Pooh back up the stairs.

The animals in the stories have human characteristics and their affectionate interaction echoes the tie between father and son. Although the book is categorized as a children's book, it also connects with adults. Most six year-olds would require that an adult read it aloud to him or her. A. A. Milne stated in his Autobiography (pps. 285-286), “The animals in the stories came for the most part from the nursery.  My collaborator [his wife Daphne] had already given them individual voices, their owner by constant affection had given them the twist in their features which denoted character, and Shepard drew them, as one might say, from the living model ... I described rather than invented them.  Only Rabbit and Owl were my own unaided work."