Ernest Howard Shepard’s Original Drawings of Winnie the Pooh – Design You Trust

Ernest Howard Shepard’s Original Drawings of Winnie the Pooh


The following illustrations are from the Sotheby’s catalogue for the auction of 42 items, titled “That sort of Bear”: E.H. Shepard’s Winnie-the-Pooh from the Collections of Stanley J Seeger and Christopher Cone. This auction was held at New Bond Street in London on December 17, 2008.

Ernest Howard Shepard was born in London in 1879 and was encouraged to draw from a young age by his artist mother. He received a scholarship to the Royal Academy at the age of 18. In the early 20th century, Shepard found success with illustrated editions of Dickens and Aesop’s fables, and his drawings were published in Punch Magazine starting in 1907, where he eventually became a permanent employee in 1921.

During World War I, Shepard served in the Royal Artillery and earned a Military Cross for bravery in France and Belgium, but he continued to create humorous sketches that he submitted to Punch. In the 1920s, he was introduced to Alan (AA) Milne, who commissioned Shepard to create line drawings for a children’s book that Milne had written. This collaboration led to the creation of the beloved character, Winnie-the-Pooh.

h/t: flashbak

He nodded and went out …and in a moment I heard Winnie-the-Pooh
– bump, bump, bump – going up the stairs behind him.”


…”What do you see there?”
“Tracks,” said Piglet. “Paw-marks…”


“What?” said Piglet, with a jump.

“Do You See Piglet? Look At Their Tracks!”

“…there was a little left at the very bottom of the jar,
and he pushed his head right in…”


“With these few words he went on tracking, and Piglet,
after watching him for a minute or two, ran after him…”


“…Christopher Robin finished the mouthful he was eating
and said carelessly: “I saw a Heffalump to-day, Piglet.”


“I’m not throwing it, I’m dropping it Eeyore.”

“Just the house for owl. Don’t you think so, little Piglet?”

“Lucky we know the forest so well or we might get lost.”

Piglet gets ready for the party.

The Bathmat
Christopher Robin gave a deep sigh… At the door he
turned and said, “Coming to see me have my bath?”


“Pooh!” he cried. “There’s something climbing up your back.”

“..then they went on to Kanga’s house, holding on to each other..”

“…and when Christopher Robin had nailed it on in its
right place again, Eeyore frisked about the forest…”


Tailpiece illustration to AA Milne’s ‘Wind on the Hill’

“As soon as he got home, he went to the larder; and he stood on a
chair, and took down a very large jar of honey from the top shelf.”


“…Winnie-the-Pooh lived in a forest all by himself under the name of Sanders.
“What does ‘under the name’ mean?” asked Christopher Robin.
“It means he had the name over the door in gold letters, and lived under it…”


“…there was a little left at the very bottom of the jar,
and he pushed his head right in…”


If you want more awesome content, subscribe to 'Oh, Design You Trust,' our brand new Facebook page! Trust me, you won't be disappointed.

More Inspiring Stories

Artist Imagines How History’s Most Famous Painters Might Decorate Their Homes Based On The Color Pallettes Of Their Paintings
Hillary White Puts Pop Culture in Classic Art
Photographer Jacqueline Roberts Uses 166-Year-Old Technique To Shoot Kids
Classic Album Covers Reimagined With Kittens
Modernist Swiss Style Posters by Quim Marin
Beautiful Black & White Photographs of Children Playing in Barcelona in the 1970s
Fears of Eros, Dreams of Thanatos: Sensual Illustrations by Alex Varenne
The Superb Oldskool Sci-Fi Art Works of Giorgio Comolo
Artist Makes Giant Sand Drawings That Are Between 30 And 100 Meters Wide
Rarest And Oldest Porsche: Yours For About $20 Million
This Artist Draws a Maps of the World with Just Single Line
Best Fancy Dress Runners of the London Marathon
Artist Erik Jensen Turns Used Keyboards Into Famous Works of Art
Rauf Yasit “Rubber Legz” Contorts His Body Into Impossible Positions
New York City By Martin Lewis: In The 1930s An Australian Emigree Captured The Essence Of The City
Fascinating Vintage Photos of a Batman-Themed Dance Class in New York in the 1960s
The DALL-E 2 Neural Network Has "Redrawn" Classic Paintings by Famous Artists While Preserving Their Style
A Gallery Of Stunning Photos Of Classic Range Rover Conversions
Gluten-Free Art Museum Lets You Enjoy Famous Artworks Without Gluten
12 Year Old Girl Invents An Adorable Teddy Bear That Hides IV Bags Making Infusions Less Scary To Children
We Can’t Stop Looking At These Drawings By Artists Reimagining Their Art As Famous Cartoons
Dad Shows What Would Happen If Kid’s Drawings Became Reality
Artists Combine Classical Paintings And Halloween Pop Culture
Extraordinary Photos Of The Joy And Freedom Of Childhood At A Time When It Was Normal To Play Out In The Street