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Winnie The Pooh is the cutest most lovable bear there is! You’re going to love getting outfit inspiration from these Winnie The Pooh outfits for women.
These outfits can really be worn anytime no matter where you are and what you’re doing, but they’re extra cute for wearing in the Disney parks on your vacation!
1. Winnie The Pooh Outfit For Winter
This Winnie The Pooh outfit is super stylish and will keep you warm in the winter.
She is wearing a gray Winnie The Pooh sweatshirt where he’s picking flowers, a Winnie The Pooh headband, olive green pants, white sneakers, and white socks.
Shop this look:
- Similar sweatshirt here
- Another similar sweatshirt here
- Similar headband here
- Similar pants here
- Similar sneakers here
- Similar socks here
2. Winnie The Pooh Cardigan Outfit
This outfit is perfect for a spring day when it’s warm, but not super hot outside.
She is wearing a yellow Winnie The Pooh cardigan, Winnie The Pooh Minnie ears, white shorts, white sneakers, Winnie The Pooh socks, and a Winnie The Pooh Loungefly backpack.
Shop this look:
- Similar ears here
- Similar cardigan here
- Similar shorts here
- Similar socks here
- Similar sneakers here
- Backpack here
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3. Pooh Bear Outfit For Cold Weather
I am living for the hat in this outfit! It looks so cozy and amazing to wear on a cold or rainy day.
She is wearing a Winnie The Pooh bucket hat, a green Winnie The Pooh sweatshirt, brown pants, and brown boots.
Shop this look:
- Similar hat here
- Another similar hat here
- Similar sweatshirt here
- Similar pants here
- Similar shoes here
4. Colorful Pooh Bear Outfit
This fun outfit is Winnie The Pooh ears, a yellow cardigan with honey bees on it, a Winnie The Pooh shirt, high waisted jeans, a Winnie The Pooh bag, and white sneakers.
Shop this look:
- Similar ears here
- Similar shirt here
- Another similar shirt here
- Similar cardigan here
- Similar jeans here
- Similar bag here
- Similar sneakers here
5. Winnie The Pooh Summer Outfit
This Winnie The Pooh inspired outfit is really cute and trendy!
She is wearing a striped Winnie The Pooh shirt, black high waisted shorts, yellow sandals, and an Eeyore backpack.
Shop this look:
6. Pooh Bear Flower And Garden Festival Outfit
This Disney outfit was worn for EPCOT’s Flower And Garden Festival. I love how she took her picture with the big yellow sunflowers since they’re the color of Pooh Bear!
She is wearing flower Minnie ears, a yellow Winnie The Pooh shirt, white shorts, a Winnie the Pooh Loungefly backpack, Winnie the Pooh socks, and white sneakers.
Shop this look:
- Similar shirt here
- Similar ears here
- Similar backpack here
- Similar shorts here
- Similar socks here
- Similar sneakers here
7. Winnie The Pooh Christmas Outfit
If you’re heading to Disneyland or Disney World during the Christmas season, then this is the outfit for you!
She is wearing Winnie the Pooh ears, a Christmas Winnie the Pooh cardigan, a black turtleneck, black faux leather pants, and black and white sneakers.
Shop this look:
- Similar ears here
- Similar sweater here
- Another similar sweater here
- Similar turtleneck here
- Similar pants here
- Similar sneakers here
8. Pooh Bear, Tigger, And Piglet Outfits
These besties wore outfits for Pooh Bear, Piglet, and Tigger. I’m not sure there’s a cuter trio to dress up as! Piglet is wearing Piglet ears, a light pink long sleeve shirt, hot pink overalls, and white sneakers.
Winnie The Pooh is wearing Pooh Bear ears, a green Pooh Bear sweatshirt, a Pooh Bear purse, camel colored pants, and black booties.
Tigger is wearing Tigger ears, a gray Tigger sweatshirt, a Tigger purse, jeans, and white sneakers.
Shop this look:
- Similar Piglet ears here
- Similar Pooh Bear ears here
- Similar Tigger ears here
- Similar Pooh Bear sweatshirt here
- Similar Tigger sweatshirt here
- Similar pink overalls here
- Similar pink top here
- Similar Pooh Bear purse here
- Similar Tigger Purse here
9. Piglet Disneybound
This Piglet Disneybound is light pink Minnie ears, a Piglet shirt, pink striped pants, and a blue scarf.
Shop this look:
10. Cute Pooh Bear Outfit
This Winnie The Pooh outfit is Winnie the Pooh ears, a yellow Winnie the Pooh cardigan, a red shirt, and a Pooh Bear Loungefly backpack.
Shop this look:
11. Winnie The Pooh Jumper Dress Outfit
Shop this look:
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12. Winnie The Pooh Halloween Outfit
If you love Winnie the Pooh, then this is the outfit for you to draw inspiration from!
She is wearing a maroon Halloween Pooh Bear sweatshirt, mustard Minnie ears, jeans, a Winnie the Pooh bag, and white sneakers.
Shop this look:
- Similar sweatshirt here
- Another similar sweatshirt here
- Similar ears here
- Similar jeans here
- Similar bag here
- Similar sneakers here
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