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…”


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