Why EH Shepard drawings are rising in value

Winnie-the-Pooh illustrator EH Shepard is having a bit of a moment.

On Tuesday, the 1926 map of Hundred Acre Wood he created for the first book featuring the eponymous bear sold for £430,000 ($568,339).

That result is three times over its estimate. In fact, it’s now the most valuable book illustration ever sold at auction.

But the result hasn’t come out of nowhere.

Prices have exploded for Shepard’s work over the past few years. Illustrations typically sell for in excess of $120,000. 

Let’s take a look at why that might be.

New old finds

Shepard’s work is not all that rare.

He was a prolific illustrator and was highly collectible in his own lifetime. You can find records of sales going back to the 1920s.

EH Shepard Map

This map appeared in the first Winnie-the-Pooh book (Image: Sotheby's)

But that’s precisely why his most desirable works are so sought after.

Most (including this map) have been locked up in private collections for decades. They are only now starting to appear on the market in significant numbers as families seek to liquidate collectors’ assets.

A key Shepard work is a prize and there is plenty of competition out there to own one.


Winnie-the-Pooh has entranced children (and parents) since it was first published in 1926. It’s also been regularly updated for new generations; with cartoons, movies and even video games.

All (save for the unsettling Soviet version) have stayed true to Shepard’s wonderful drawings.

That’s quite remarkable when you think about it. By and large, once things are remade, there is a move towards reinvention of some kind.

EH Shepard Winnie-the-Pooh

Shepard's drawings instantly take us back to childhood (Image: Sotheby's)

But Shepard’s drawings are critical to the appeal of the stories.

It’s the same reason illustrations by Tintin artist Herge are going through the roof. Both are iconic and integral to the overall experience.  

Shepard and Milne worked symbiotically to bring the world of Hundred Acre Wood to life.

It was a labour of love. Christopher Robin was Milne’s son, while the cast of characters that surround him were based on his own stuffed toys.

As a result, they are remembered with great affection.


Shepard spent much of his career as a political cartoonist at Punch magazine – a British institution.

If you have a little time on your hands, check out his series on the first world war. It’s both deeply funny and achingly moving.

Shepard saw himself as a serious artist.

As a result he was always dismissive of his work on Winnie-the-Pooh, seeing it as little more than a side gig.

But I’d argue that it was one of his finest hours.  

The drawings are charming without being saccharine.

They have a timeless quality that few other illustrators could have matched.

You can't argue with that kind of a legacy. 

All the best,


PS. If you’re interested in owning an excellent example of Shepard’s early work, I have just the thing.

Featured products

Elvis Presley Authentic Strand of Hair
Elvis Presley Authentic Strand of Hair
Sale price£399
In stock
Fidel Castro signed certificateFidel Castro Signed Certificate
Fidel Castro signed certificate
Sale price£2,995
In stock
King Henry VIII Autographed DocumentKing Henry VIII Autographed Document
King Henry VIII Autographed Document
Sale price£55,000
In stock