Classic Winnie the Pooh & Friends Checks   Recently updated !


classic winnie the pooh and friends checks

Classic Winnie the Pooh and Friends checks celebrate the gentle charm and timeless warmth of the Hundred Acre Wood. This six-design series features beloved characters including Winnie the Pooh, Piglet, Tigger, Eeyore, and friends, illustrated in soft, storybook-style scenes that feel familiar and comforting. The designs use light, cheerful backgrounds and expressive character moments that reflect the quiet humor and heart of the original stories.

For many longtime fans, this series replaces the earlier “Classic Winnie the Pooh” check designs that were available years ago and are no longer in print. While the artwork is not identical to the original classic set, it carries the same spirit, tone, and character focus that made those designs so enduring. This updated collection offers a thoughtful way to continue enjoying Winnie the Pooh checks today, while staying true to the look and feeling that fans have loved for generations.

These checks are especially well suited for longtime Winnie the Pooh fans, gift buyers, and anyone who prefers a softer, storybook style for everyday use.

Matching Checkbook Cover

The matching checkbook cover features a cheerful scene from the Hundred Acre Wood, with Winnie the Pooh and friends gathered beneath a leafy tree. The Winnie the Pooh checkbook cover can be added when ordering the checks, or purchased on its own by clicking the image above.

Matching Address Labels

The matching address labels feature the same six Winnie the Pooh and Friends designs shown in the check series, each highlighting a different character moment from the Hundred Acre Wood. The Winnie the Pooh labels can be added when ordering the checks, or purchased on its own by clicking the image above.


The original classic check design

Old “classic winnie” design is no longer available.


Established in the 1920’s, Winnie the Pooh has been a Disney character that has been loved and cherished by many. Re visit Hundred Acre Wood and Pooh, Tigger, Eeyore, Piglet, and Christopher Robin with the classic Winnie the Pooh check series.

Four designs feature the A.A. Milne characters loved by young and old alike on pretty pastel backgrounds.

“Some people talk to animals. Not many listen though. That’s the problem.”
― A.A. Milne, Winnie-the-Pooh