One of my all-time favorite characters to disneybound as is Winnie the Pooh. There’s just something so lovable about our favorite bear! I love planning Winnie the Pooh Disneybound outfits because his two colors, red & yellow, are so bright and always make for such fun outfits! While I’ve done two Winnie the Pooh Disneybound outfits in the past, this one I put together is by far my favorite!
What sets this look apart is all of the accessories! I wanted to prepare a complete Winnie the Pooh Disneybound that would stand out and make for a great outfit to wear to the Disney parks.
I’ve linked all of the outfit details so you can shop the entire look or pick out your favorite pieces. I hope this outfit inspires you to plan a Winnie the Pooh Disneybound because it’s so much fun dressing as our honey-loving friend!
You can’t have a Winnie the Pooh Disneybound outfit without the perfect shirt, and this “Oh Bother” shirt from Marlee Mae Everyday perfectly represents Pooh bear. I love the bright yellow color of the shirt and how the “Oh Bother” is in red glitter! This shirt is perfect to wear with everyday outfits or to wear to Disney parks. You can shop the shirt here. Use code CHELSEY15 to save 15%.
You have to have red in your Winnie the Pooh Disneybound, and this red skater skirt adds that perfect pop of color to this outfit! If you know me at all, you know I LOVE wearing skirts for my Disney outfits. This skirt is only $25, and you can restyle it so many ways. My closet is full of colorful skater skirts because they so easily pair with Disney tee’s! You can shop this red skirt here or you can shop all my favorite skirts here.
This Tsum Tsum Winnie the Pooh headband is so adorable I can’t even handle it! What I love most about it is that it not only displays Pooh bear, but it also has Tigger on there too! So you could really wear it for Winnie the Pooh outfits AND Tigger outfits. Now that I have this headband, I want to plan a Tigger Disneybound outfit (I’m all about restyling pieces and saving that money!) You can purchase this Winnie the Pooh headband here for only $15.
These red heart sunglasses add that glamorous touch to this Winnie the Pooh Disneybound outfit. Probably my favorite reason to incorporate sunglasses into Disney outfits is because depending on the lighting, sunglasses can end up saving the day when it comes to pictures. Let me explain… When you’re exploring either Disney World or Disneyland, most of the time it’s going to be bright and sunny. Which is great for weather but bad for pictures. The harsh lighting can cause awkward shadows on your face when trying to get those cute outfit pics for the gram. So I always recommend bringing a pair of cute sunnies that are way more flattering in direct sunlight. You can shop these red heart sunglasses for only $10 here.
For lovers of Winnie the Pooh, this adorable bee necklace adds that perfect touch to any outfit! What I love most about this necklace is how simple and subtle it is. It’s perfect to wear with a Winnie the Pooh Disneybound outfit or just to style with everyday outfits. You can buy this bee necklace for only $10 here.
To complete this Winnie the Pooh outfit, this Winnie the Pooh phone case and matching PopSocket make for the perfect accessory! I love how the matching PopSocket is included because normally I avoid putting a PopSocket on because I’m afraid it won’t match my phone case. You can purchase both of these for only $15 here.
I hope you loved this Winnie the Pooh Disneybound outfit! I had so much fun putting it together, and I can’t wait to show it to Pooh bear himself on my next Disney trip! I’ve included all the outfit details below as well as some other adorable Winnie the Pooh accessories. I can’t wait to see your Winnie the Pooh Disneybound outfits!
Shop the Outfit:
Shirt: Marlee Mae Everyday $27 – Save 15% with code CHELSEY15
Skirt: Marlee Mae Everyday $25
Headband: Marlee Mae Everyday $15
Sunglasses: Marlee Mae Everyday $10
Necklace: Marlee Mae Everyday $10
Phone Case: Marlee Mae Everyday $15
Other Pooh Bear Merch
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