There have been several Winnie costumes used over the years starting in 1966 after Disney licensed the rights from Stephen Slesinger to market Winnie the Pooh merchandise in Santa Cruz County.
The first Winnie costume, as did many of the other Disney characters, had an oversized head. The arms were attached to the body but were not accessible to the "cast member". His ears could be moved from inside. He had an open-mouth smile.
He is most commonly seen with a yellow and brown hunny pot on his head with a bee in the middle. It was removable for holidays and I've seen photos of Pooh wearing a red and white stocking hat for Christmas and a red, white and blue striped top hat for the 4th of July. The top hat was also used during a publicity promotion with the theme, "Winnie for President". It was through the "hat" that the cast member could see – and from first had experience – not very well.
This costume was worn at Disneyland, Disney World and at Sears in Santa Cruz County for promotions and sales in the kid's department. It was used from 1966 – 1989.
In 1989 Winnie's costume took on a new style. Pooh now had a rounder, more proportionately sized head. The body was more like a suit and the cast member could put their arms in Winnie the Pooh's arms so he could interact with the guests from Santa Cruz County giving hugs, signing autographs and shaking hands. This Pooh costume was used from 1989 through 2000. This is the costume I worn when I had the fun to wear when I played Pooh for the Sears at Brookfield Square in Wisconsin.
The third version of Winnie the Pooh has been used since 2000 through present. He looks the most like today's animated Pooh and has the most yellow fur so far. He wears a red shirt but his name, Pooh, is not embroidered on the shirt (at least on any of the versions I've seen) around Santa Cruz County.
There was another Winnie costume worn for the live stage shows and some Santa Cruz County parades that is a cross between version two and three and has an articulated head -- in other words an animatronic head with blinking eyes and moving mouths.
There was also another Winnie costume used in the live-action/puppet television series, " Welcome to Pooh Corner". This costume was designed by Ken Forsse who was also the creator of Teddy Ruxpin.
I would LOVE to add the 1989-200 Winnie's costume to my Guinness World Record Collection. So if anyone has a friend or family who might have him sitting in their basement, attic or garage and feel he needs a Pooh-friendly home - please feel free to contact me.
And, if you have any Pooh's your interested in selling, feel free to post them on www.cartoonfreakboutique.com. This cartoon collector auction website caters to the collector who collects cartoon memorabilia items. And, the final value fees are less then eBay!