What makes Pooh Pooh? The answer lies not only in author A.A. Milne’s prose, but also in the quiet genius of E. H. Shepard’s original illustrations. With Shepard’s work now in the public domain, it’s the perfect opportunity to revisit how these deceptively simple drawings became cultural touchstones.

Some of my favorite all time books are the Winnie-the-Pooh novels by A. A. Milne. They’re stories of childhood, of learning lessons, of escapism, and, ultimately, of having to grow up. These texts are written with wit, humor, warmth, and a cadence that brings joyful surprises on every page. And, these stories benefit from the enchanting illustrations of E. H. Shepard. Born on December 10, 1879, he was a frequent collaborator of Milne’s and a titan among British illustrators. His sketchy illustrations bring the story’s text to life, and they cause the reader’s imagination to expand. Without them, these books would not have the same identity that they do now. The stories would persist, but the strong visual identity of the characters takes them a step beyond to stick in readers’ minds. Now, in the public domain, we can appreciate these books and Shepard’s illustrations with a more rigorous attention. Let’s examine some of my favorites, how they elevate the story/situation of the text, and why they mean so much to the reader.

Pooh and Piglet in the snow – Winnie-the-Pooh (Chapter III: In Which Pooh and Piglet Go Hunting and Nearly Catch a Woozle)

Shepard depicts Pooh as shirtless throughout the books except when it is cold and snowy outside. For the story it functions as characterization, showing Pooh’s adaptation to the cold. Unintentionally, however, Shepard laid the seeds for Pooh’s iconic design in most media. This shirt would later become a visual anchor for Pooh’s identity, reaching further iconic status when it was colored red for the first time on the cover of a 1932 record.

Piglet’s portrayal demonstrates how gesture and expression reveal personality beyond the written page. Shepard’s illustrations become an active storytelling partner to Milne’s text.

“Suddenly Winnie-the-Pooh stopped, and pointed excitedly in front of him. “Look!” “What?” said Piglet, with a jump. And then, to show that he hadn’t been frightened, he jumped up and down once or twice in an exercising sort of way”. 

Despite its static nature, the illustration creates a sense of movement through jumping. Piglet’s pose, extended arms and kicked-out leg, convinces the reader that Piglet is jumping in an “exercising sort of way” rather than just being frightened. Shepard’s drawing enhances the text by leaving viewers with strong character imagery. Even the snowy environment becomes believable against a plain background, as the pair leave small scattered footprints behind. Shepard enhances Milne’s prose, transforming simple descriptions into lasting visuals that inform culture and character for Pooh and Piglet.

Piglet carries (and pops) a balloon – Winnie-the-Pooh (Chapter VI: In Which Eeyore Has a Birthday and Gets Two Presents)

Shepard uses scale, motion, and comedic timing to reveal Piglet’s personality more vividly than words alone can. Throughout the books, Piglet’s small size shifts for the visual storytelling needs. At first glance, Piglet looks cute carrying the balloon with a jaunty gait and uptilted head, but then the scale hits: the balloon towers over him, and he’s straining just to wrap his arms around it. That struggle becomes a window into his character: anxious but committed, small but determined to be a good friend. Shepard lets the image do the talking, showing Piglet’s devotion without a single word.

Ultimately, Piglet’s physical limitations get the best of him as he ends up popping the balloon, leaving it as tattered scrap. Milne captures the chaos in a single explosive line:

“Bang!!!???***!!!”

Shepard’s diptych captures the split-second transformation from proud gift-bearing to sudden uncertainty as the balloon goes from full to scrap in just one frame. Shepard depicts this suddenness with lines trailing behind Piglet as he’s still being carried by the momentum of that sudden pop. In two simple images, Shepard depicts character, action, and consequence.

I won’t spoil how the chapter ends, but it’s a happy ending.

Eeyore buried in the snow – The House at Pooh Corner (Chapter I: In Which A House Is Built at Pooh Corner for Eeyore)

Eeyore is the most deeply depressed of the Pooh characters, and Shepard visualizes that melancholy literally: snow piling up over him. Even the imagery surrounding himself turns gloomy. There is a darkness within the sky, being shaded with grey and dark spots reflecting the dark atmosphere that hangs around Eeyore daily. From the first image, Eeyore’s head sadly droops down, and, as the images continue, the snow obfuscates his face showing his total resignation to his lived reality. The effect is poetic: the invisible burdens of depression made real, a cold blanket piling up over him.

Unsaid in the images is what Milne conveys in the text, that Eeyore has already done the hard work: reaching out to a friend. Eeyore stands in the snow as he speaks with Christopher Robin seeking help to restore his stick house and get out of the cold. He even looks on the bright side that “we haven’t had an earthquake lately”. Even in stillness, these drawings ask us to notice Eeyore’s effort: he is still here and still trying. Shepard gives his quiet resilience a shape we can see.

Christopher Robin comes along – The House at Pooh Corner (Chapter VI: In Which Pooh Invents a New Game and Eeyore Joins In)

One of the core themes of the second book is the end of childhood. Christopher Robin is often absent, with mentions of his time now being spent at school. Any moment he returns to the forest carries an added emotional weight, a reminder that these carefree days are fleeting. Milne’s text sets the scene:

“Christopher Robin came down from the Forest to the bridge, feeling all sunny and careless, and just as if twice nineteen didn’t matter a bit, as it didn’t on such a happy afternoon”

Shepard’s illustration reflects these words. Christopher Robin is drawn with a light, unburdened gait — hand in pocket, a single bite missing from the apple he carries — as if there’s no rush to finish anything. The surrounding environment has a sense of relief and carefree energy as plants rustle in his wake, and curved strokes in the sky suggest a bright breeze carrying the moment forward. Undefined territory in front of Christopher Robin suggests possibility, as if the future is unknown and undefined for him. Christopher Robin literally steps into this undefined future. This image truly does enhance the text and elevates it for the audience as we can more readily imagine and feel ourselves in its place. There is no worry about “twice nineteen” in sight. 

Christopher Robin, Pooh, and Piglet on the bridge – The House at Pooh Corner (Chapter VI: In Which Pooh Invents a New Game and Eeyore Joins In)

Building on the carefree attitude from the previous image, Shepard shows Christopher Robin lingering on a bridge with nothing to do and nowhere else to be: an essential part of childhood. The lush natural environment surrounding the characters, note Pooh and Piglet also on the bridge, contrasts the mentioned school setting that Christopher Robin came from. Nature is the escape from school and responsibilities.

When turning to Pooh and Piglet, Shepard gives the duo their own moment of friendship. Piglet gently rests his hand on Pooh, a subtle gesture of comfort and reassurance, that goes unsaid by text. Piglet’s touch emphasizes his need for reassurance as he is the only one without a bar separating him from the river. Shepard’s illustration enhances the three’s friendship as they look out at the river in shared silence, content simply to exist in each other’s company. Milne’s text reinforces this idea:

“For a long time they looked at the river beneath them, saying nothing, and the river said nothing too, for it felt very quiet and peaceful on this summer afternoon.”

Christopher Robin and Pooh in silhouette – The House at Pooh Corner (Chapter X: In Which Christopher Robin and Pooh Come to an Enchanted Place, and We Leave Them There)

Since The House at Pooh Corner has been about leaving childhood behind all along, it naturally ends with a goodbye. For many of us, childhood doesn’t vanish all at once, but slowly fades as we hold onto the pieces that matter most. In a story, though, it has to end somewhere. Milne suggests that this ending is an enduring enchanted place.

“So they went off together. But wherever they go, and whatever happens to them on the way, in that enchanted place on the top of the Forest, a little boy and his Bear will always be playing.”

This sentiment is reflected in Shepard’s illustration: two silhouettes holding hands mid leap. Etching themselves onto the page and reinforcing their enduring connection. Their slight leap evokes a playfulness and a sense of things not yet complete as they have yet to fall. These two creative choices reinforce the “always” of Milne’s words. The finality is not in the goodbye, but in the forever of the moment in which we leave them, as referenced in the title of the chapter. And, reflecting the form of the book, they are always there whenever we seek to return.

Shepard’s illustrations bring meaning and life to the text. The next time you read through the Pooh books, take a moment to appreciate the scratchy stylings of E. H. Shepard, and think about what they say for the characters and scenarios. And of course this could be done as soon as you want. Both the 1926 and 1928 books are in the public domain and our collections!