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Winnie the Pooh and Friends Join the Boo Crew for Halloween

By Alison | Updated on August 20, 2026

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

The Hundred Acre Wood is looking a little more haunted! New Winnie the Pooh Halloween merchandise has arrived HERE on DisneyStore.com. Pooh, Tigger, Piglet, and Eeyore are ready to celebrate the sweetest spooky season ever. Winnie the Pooh and Friends Join the Boo Crew for Halloween!

Most of the collection is exclusive to the Disney Store. The exceptions are the Little Words Project bracelet, Happy Hunnyween hat, and plush Halloween countdown calendar.

Join the Boo Crew

Orange Halloween sweatshirt with Boo Crew characters and haunted house design.

The Boo Crew sweatshirt might be my favorite piece in the collection. The warm pumpkin color could not be more perfect for fall. Pooh and his friends gather in front of a haunted house beneath the words “Boo Crew.” Bats, stars, and a crescent moon add plenty of Halloween spirit.

Black Disney sweatshirt with Halloween and fall-themed characters and motifs.

There is also a dark pullover featuring Pooh and friends in a horizontal character design. It has a more subtle look for those who prefer understated Halloween style.

Tees From the Hundred Acre Wood

Kids T-shirt featuring Winnie the Pooh with a honey pot and Tigger in the back design.
Cute Winnie the Pooh Halloween T-shirt with pumpkins and ghosts for kids.

Several new T-shirts let individual characters steal the spotlight. Pooh appears on an oversized gray tee looking ready for a Halloween adventure. Tigger appears on the back of the t-shirt and looks as bouncy as ever. A women’s cream-colored tee features Pooh dressed for the season. “Winnie the Boo.” Yes, please!

Bags and Accessories

Orange tote bag featuring Winnie the Pooh and Tigger with Halloween decorations.
Cute Winnie the Pooh plush bag with strap, perfect for Disney fans and collectors.

The orange tote is practically begging to join me for a fall Disney Parks day. Pooh and his friends are dressed as the sweetest vampires I’ve ever seen! You can find him and Tigger on the front, while Piglet and Eeyore decorate the back. There is also an adorable Pooh wristlet featuring his smiling fanged face. The neutral coloring makes it easy to carry with anything!

Kids Disney cap featuring Winnie the Pooh and friends in playful design.

A character-covered baseball cap adds another option for completing your Pooh-inspired look. It perfectly matches the Vampire Tote!

A Little Extra Hunnyween Fun

Colorful Winnie the Pooh themed beaded bracelet with alphabet beads spelling 'Boo to Pooh'.

The Little Words Project “Boo to Pooh” bracelet combines black, orange, and white beads with adorable Pooh details. This is one of the few items that is not a Disney Store exclusive.

Cute Winnie the Pooh plush toy with bee costume on Halloween hat.
Cute Winnie the Pooh pumpkin plush toy with numbered sections for kids' game.

The Happy Hunnyween hat is equally adorable. A plush Pooh dressed like a bumblebee sits right on top! Finally, the plush Halloween countdown calendar makes waiting for October 31 much sweeter. Pooh holds a giant pumpkin featuring numbered pockets to count down the days.

This collection proves Halloween does not have to be scary to be fabulous. Sometimes all you need is a little Pooh, a little hunny, and your favorite Boo Crew for Halloween! This is my favorite type of Halloween!

Ready to head to Disney this Halloween season? If you’re ready to book your fall vacation to Walt Disney World, make sure to reach out to Small World Vacations. They are the preferred travel agent of Disney Fashionista. Let them know that we sent you!

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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
Latest posts by Alison (see all)
  • Winnie the Pooh and Friends Join the Boo Crew for Halloween - August 21, 2026
  • Set Your Alarm for This BaubleBar Haunted Mansion Private Access Drop - August 20, 2026
  • Run For The Boo-tiful Bling with Main Street Bella’s Haunted Ever After Virtual Race - August 20, 2026
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