Even with their faces obscured, Shepard’s drawing manages to give each character a unique sense of self — courageous Christopher Robin hangs over the top rail, while Pooh mimics his best friend below. The ever devoted Piglet gently places her hand on Pooh’s back, watching the water from a safer distance as it floats by. Nostalgia oozes from ever cross-hatched line.
The illustration is set to fetch anywhere between £100,000 and £150,000 ($159,000 and $239,000) at Sotheby’s English Literature, History, Children’s Books and Illustrations sale. In honor of the rare occasion, we’ve compiled a few more retro looks at Winnie-the-Pooh. You can take a peek at the vintage sketches pulled from the archives below.