13 Old-School Teddy Bears That Are Cute, Cuddly + Hipster-Approved

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As you browse the aisles of supermarkets and toy shops for a stuffed toy that isn’t bright purple or minion-themed, you might find yourself cursing the day you ever threw out the classic bears from your childhood. Why does every teddy bear have to look like a unicorn nowadays? Luckily, we know your struggle.

Sometimes you just want to get a teddy bear for you or your baby that’s soft and huggable, and doesn’t stick out like a sore thumb in your vintage-inspired home. Check out this list of 14 old-school style bears that are sure to tick all your boxes.

QUICK LOOK: OUR 3 FAVORITES

Kodiak Bear

kodiak bear

KidKraft Boy Naptime Teddy Bear

NAPTIME BEAR

Oitscute 2 Pack

OITSCUTE 2 PACK

Kodiak Bear

Kodiak Bear

kodiak bear

Oversized and and oh-so-soft, this Kodiak plush is as huggable as they come - your little one will love cozying up to their furry friend through the holiday season.

If Eeyore and Winnie The Pooh had a very large baby, it would look like this bear: melancholy and a little bit depressed looking, but also the cutest thing you’ve ever seen. Oversized and and oh-so-soft, this Kodiak plush bear is practically begging for a hug - your little one (or you, we don’t judge) will love cozying up to this gigantic furry friend.

It’s a statement piece - that’s for sure - but if anyone can make it work, it’s you. 

KidKraft Boy Naptime Teddy Bear

KidKraft Boy Naptime Teddy Bear

kidkraft boy naptime teddy bear

This adorable teddy bear is ready to sit next to your child and watch over their dreams! Dressed in a beige sleeping cap and pants, this boy teddy bear is made of soft, huggable polyester plush and features embroidered eyes and nose to make it safer for babies and small children.

Dressed in a beige sleeping cap and pants, this teddy bear is made of soft, huggable polyester plush and features embroidered eyes and nose (which makes it safer for babies and small children).

The little sleepy brown bear also comes with a removable beige shirt that can be embroidered with your child's name, a special date or lucky symbol, making it a perfect gift for a special occasion.

Oitscute 2 Pack 

Oitscute 2 Pack

oitscute 2 pack

Super-soft Teddy bear wearing clothes has an adorable expression, a unique mix of curiosity, mischief and fun that brings a lifetime of joy and companionship; Furry, fun plush toy is a thoughtful gift for wives, girlfriends and children.

Two are better than one - especially when it comes to fluffy little stuffed toys. These bears are perfect gifts for a couple or just as an extra special gift for your favorite little kid.

The bears themselves have the quintessential teddy design and soft, brown fur, but the clothes they wear make them unique. Pick between his-and-hers designs with one bear in a dress and the other in overalls, or choose the two bears in the vintage pastel dresses. We love that you can reflect your own style.

Bearington Baby

Bearington Baby

bearington baby

This adorable Shaggy bear has the design of a classic bear with the softness of modern plush. Measuring 11" tall in its sitting position, Shaggy is the perfect size for cuddling, and is sure to become a treasured companion.

Classically cute and scruffy with big brown eyes, this little guy is the archetypical teddy bear.

The Bearington Collection has made a name for itself worldwide for its luxurious fabrics, excellent quality and adorable designs, and we are of the opinion that everyone should get the chance to own a Bearington Bear. How could you resist that little face and plaid bow?

Vermont Teddy Bear 

Vermont Teddy Bear

vermont teddy bear

It's hard to imagine how they could be any cuter, but our Soft & Cuddly Vermont Teddy Bears are simply too adorable when dressed up in colorful clothes and costumes. Their huggable construction makes them the perfect gifts for Kids and Teddy Bear lovers everywhere, whether it’s a birthday, baby shower, holiday or first day of school.

The great thing about Vermont Teddy Bears is that they’re made to last. They aren't some one-use, factory-made products: they’re made with love in Vermont from 100% recyclable stuffing and come with a lifetime guarantee. We love this, because it means you can pass the bear down multiple generations.

Made with smooth, silky fur these 13” bears are simple, classic and extremely huggable.

Vintage Rose Teddy Bear 

Vintage Rose Teddy Bear

vintage rose teddy bear

This 10" teddy features the vintage rose pattern from Little Me and is perfect for baby's every adventure. Once the playtime fun is done, this cuddly companion coordinates perfectly with nursery décor or matching Little Me clothing and accessories.

GUND teamed up with classic baby apparel brand Little M to create the vintage teddy of our dreams. Made with a delightful rose pattern that reminds us of our Grandmother’s wallpaper, this medium-sized bear is the perfect combination of style and comfort.

The rose pattern coordinates perfectly with vintage-themed nurseries.

Bearington Hudson

Bearington Hudson

bearington hudson

Hand crafted using the most luxuriously soft plush, this classic teddy bear is perfect for everyone from the collector to a special child in your life.

This adorable Hudson teddy bear has the style of a classic bear with the softness of modern plush materials. Hand-crafted using super soft plush, this classic teddy bear is perfect for everyone from the bear collector to your own kids.

Founded in 1997, Bearington has got more design awards than any other teddy bear company - so you know their bears are going to be good.

Oitscute Small Baby 

Oitscute Small Baby

oitscute small baby

This Teddy is a soft and huggable 10 inch companion that's always ready for naptime, playtime, and any time in between.

Any little girly-girl will go absolutely mad for these cute baby bears dressed in vintage dresses. There are six styles to choose from, so you can easily find one in your favorite color.

We’ve got our eye on the little bear in the pink lace dress with the pet rabbit, because what is cuter than a toy with another mini toy?

Oiscute big baby 

Oitscute Big Baby

oitscute big baby

Big teddy bear, brown/pink teddy bear wearing pink, white, red, purple, blue dresses. The clothes have very good workmanship.

There’s something extra comforting about having a bear big enough to cuddle, and the Big Baby from Oitscute is one of those toys. This is a soft, retro-style bear with fluffy fur, a hand stitched nose, satin bow, and it comes wearing a vintage pink, red, white, purple or blue dress with little hand stitched details.

It’s an all-rounder in the world of teddy bears - we would still like to have a bear like this!

Coco Bear 

Coco Bear

coco bear

Aurora World's Coco Bear is covered in shaggy, super-soft plush and wears a dark red ribbon bow. It has lock-washer eyes for safety and double-bagged bean filling. Aurora World is an industry leader with over 30 years of experience designing and manufacturing innovative, high quality plush products.

Aurora World's Coco Bear is covered in shaggy, dark brown plush and wears a red ribbon bow around its neck. Since it is in a seated position, this bear would be better suited to being a decorative feature than for actual cuddling - but the super soft fur might make you think otherwise. It would also make a great gift!

Bearington Baby’s Big Blue Bear

Bearington Baby's Big Blue Bear

bearington baby's big blue bear

Hand crafted using the most luxurious, soft plush, the "Baby's First Blue Teddy Bear" is sure to become baby boy's favorite. Measuring 18" tall, this blue teddy bear is the perfect size to accent any baby room.

In the classic teddy bear shape with a bright pastel blue color, a bear like this is a must-have for any nursery. It’s ridiculously soft, fluffy and bigger than normal teddy bears. And it also says ‘Baby’s First Bear’!

The embroidered eyes ensure safe use for all ages.

Brown Christmas Bear

Brown Christmas Bear

brown christmas bear

Cozy and cute, a stuffed brown bear doll featuring a panel stitched label accent with a red and white striped scarf detail.

It looks like the kind of bear you would find in the opening scene of a Christmas tale from the 1920’s - and that’s why we love this toy.

It literally could not get more vintage-looking with it’s dappled brown fur and stitched Christmas label. The cherry on the top is definitely the little red and white striped scarf.

Cody Bear

Cody Bear

cody bear

This Ty Attic Treasure - HEARTLEY The Bear is originally from the 90's and is approximately 12" large.

Ty Attic Treasures Heartley the bear is originally from the 90s, so we highly recommend you take any chance you get to buy this classic teddy if you like collecting vintage things.

There’s something particularly endearing about this bear - it's so little and frazzled looking that it takes you straight back to your childhood.

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