Winnie the Pooh - Cowboy - Pooh Professions

This charming pin features Winnie the Pooh dressed as a cowboy, complete with a brown hat and a red neckerchief. Released in 2005 as part of the Pooh Professions - Cast Lanyard Series 3, this design celebrates the whimsical nature of the beloved bear from A.A. Milne's classic stories, first adapted by Disney in the 1966 featurette Winnie the Pooh and the Honey Tree. Winnie the Pooh, created in 1926, remains one of the most iconic and enduring characters in Disney history, often appearing in various costumed roles for pin collectors. As an Open Edition pin originally released at Disneyland Resort, it was primarily available to guests through the Cast Member lanyard trade program. The Pooh Professions series is a highly nostalgic collection for long-time traders, as it showcases the character in various playful occupations. The design is simple yet effective, highlighting Pooh’s friendly face set against a textured, dark background. Because it is an Open Edition pin, it served as an accessible entry point for many early collectors building their collections at the parks. Its status as a lanyard series pin makes it a fun piece of Disney trading history, capturing the spirit of the park-exclusive trading culture of the mid-2000s. Collectors often seek out these specific professions to complete the set or to add a touch of western flair to their Winnie the Pooh displays.