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The Disney Fashionista

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Whimsical Winnie the Pooh Inspired Looks

By Alison | Updated on June 18, 2025

Please note, some posts on Disney Fashionista may collect a share of sales, if you decide to shop through our links

Winnie the Pooh and his friends in the 100 Acre Woods never go out of style. Originally written in 1926, throughout the years, I daresay he’s gained even more popularity! From Classic Pooh to his Modern design, enjoy whimsical Winnie the Pooh inspired looks with new exclusive merchandise on The Disney Store website.

Wear your stripes as proudly as Tigger himself with the themed unisex shirt. Or when all the bouncing wears you out, opt for the sweet nightshirt featuring Tigger sprawled on a crescent moon. Pooh, on the other hand, is not up for bouncing. He lazily declares on the pink sweatshirt, “Nothing is my favorite thing to do.” I feel you, Poohbear. We all have those days, and this is just the top to wear for them! The sweatshirt is also a Disney Store exclusive. Lastly, a lady’s semi-crop top rounds out the new apparel with embroidery of the forest friends hanging out together. Whether you’re bouncing or doing nothing, this tee declares “It’s always better together.”

Three denim and “suede” bags slide online for a Disney Store Exclusive. Winnie the Pooh’s drawstring backpack declares “Stuffed with Fluff” aka all your important items! Meanwhile, Tigger’s Crossbody bag features adorable stripes, like him. The roomy bag and coin purse sum up Tigger’s attitude with the phrase, “Feel like Bouncing.” It’s no coincidence that the smallest bag features the smallest friend of the group. Finally, a shy Piglet gazes at a “Hunny” bee on the front of the belt bag.

Be still, my heart! I wore a Winnie the Pooh dress on the first day of kindergarten, and this is totally the kind of lunchbox I carried! The tin boxes aren’t in widespread production anymore, but they’re perfect for nostalgic display or to store your trinkets. You’ll only find the Winnie the Pooh and Pals Tin lunch box at The Disney Store.

Enjoy the whimsical Winnie the Pooh inspired looks when you shop the collection HERE. Which is your favorite piece? Drop us a comment below and let us know!

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Alison
Alison
Alison grew up in Orlando and attended Disney often.Some of her best childhood memories were created on Main Street.Her favorite princesses, Olivia and Savannah call her mom (but her favorite Disney princess is Snow White.
Alison
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