The Wonderful World of the Teddy Bear (Fourth Edition)


Of course, I couldn’t do Valentine’s Day without including the iconic Teddy Bear. For decades this cuddly toy has been adored by children and adults alike. And you’d often find this little guy as a popular V-Day gift from sweethearts around the world. Since they have movable arms, you often see them dressed in all kinds of little costumes. Since they’re so irresistibly cute, you’d often find them dressed for all kinds of occasions and holiday. But once in awhile, you’ll see a teddy bear dressed as a pop culture icon or culture figure. So for your reading pleasure, I give you another assortment of adorable teddy bears. Enjoy.

  1. “One of you will beartray me..”

DaVinci’s The Last Supper with bears. From the Jeju Island teddy bear museum.

2. Mama bear needs a new pair of shoes.


This bear is supposed to frequent a casino. And it seems she’s got all hearts.

3. All bears on deck.


This is from a teddy bear museum, possibly in the UK. Nonetheless, the wooden ship is amazing.

4. Erin has always been an Irish darling.


She’s supposed to resemble an Irish river dancer for Saint Patrick’s Day. Love the shamrock head garland.

5. Seems like our bear archaeologists found something incredible.


These bears have came to the tomb of Emperor Qin Shi Huangdi. Here they marvel over remains of some terra cotta soldiers.

6. Here they stand on the ruins of war.


These are teddy bear soldiers near ruins in France during WWII. And yes, some hang out in a jeep.

7. The band played on….


This is a teddy bear rendition of the sinking of the Titanic. Cue to the polar bears on the iceberg.

8. A flower dress is perfect for any spring occasion.


She even has a lace handkerchief in her paws. Love her flowery hat.

9. Coco always has to be a fashionista.


She wears a kimono to go with her red handbag and sunglasses. While her bag is from Big Brown Bear.

10. Perhaps you’ll appreciate this birthday bear.


This one has a bikini clad bear coming out of the cake. Kind of amusing and adorable.

11. Bet you’ve never seen a bear in his boxer briefs.


His waist band says it all. And he looks so adorable in that pose.

12. Graduation is always quite an accomplishment.


This graduate is in white for the Class of 2015. So its job prospect might not be great.

13. On Halloween night the pumpkin fairy appears.


It has orange wings and a jack-o’-lantern magic wand. Doesn’t look spooky. But is quite adorable.

14. Mary can always spare a put or two.


She’s supposed to be a female golfer. Here she wears a skirt with her diamond polo.

15. David always knows how to make a goal.


Since he’s got claws, he needs no cleats. But let’s hope they don’t rupture the ball.

16. Ryan will just shoot some hoops.


He also knows how to dribble. So you might not want to play a round of one-on-one with him.

17. Brittany knows how to look chic in pink.


She even wears a camo denim outfit and a pink leather jacket. So cute.

18. Anyone miss Bearack Obearma yet?


Indeed, I sure do miss him and his presidency. Still, he comes with Obearma Care.

19. This your Captain Clawly Clawenberger speaking.


This teddy bear’s supposed to be an airplane pilot. Will fly you to the moon and warm your heart.

20. Watch out for this grizzly pirate.


He’s even got an eyepatch. But back away when he uses his sword.

21. Nancy Bear is on her way to the spa.


She’s in her pink robe with a towel around her head. So she’s good to go.

22. Barry is all ready for the big game.


He’s already got his shoulder pads on. Not sure why he’s not wearing a helmet.

23. Christmas is the time to shine in a Santa dress.


She’s even wearing a Santa hat. So pretty and festive.

24. A bear should always look chic on the town.


she wears a dress with an iconic Vuitton print. Or is it Gucci? Who cares?

25. Ethan is Army strong.


He’s wearing a desert camo uniform. Wonder if he’s served in Afghanistan.

26. Father Christmas is the bearer of great tidings.


He’s the British equivalent to Santa Claus. But check out that cane and kick ass cape.

27. A distinguished Pilgrim always has a goatee.


He’s a Thanksgiving bear. Wait until he takes the land away from the Indians.

28. A Christmas angel wishes peace on earth.


She even has red bird in an intricate design. Love her blue dress.

29. When there’s snow, bring snow shoes.


He’s even all bundled up. Despite that bears usually sleep in during the winter.

30. Tape measure can also double as ribbon.


Though she also uses it to measure sizes. Still, so adorable.

31. This Steiff bear makes his own in his workshop.


Didn’t know he could have his own toy workshop. Includes a sewing machine and wood stove.

32. This alien teddy bear is out of this world.


IT’s red with a little space helmet. It’s also a limited edition Steiff from Japan.

33. A colorful harlequin also needs to know how to juggle.


He’s in red and white. while he wears a cone hat of green and blue.

34. Charlotte always loves to dress in a scary costume for Halloween.


She wears a black bat mask and a black tutu. She’s even got a spider near the skirt.

35. A red dress and tiara makes a bear queen of the ball.


She’s even got a bouquet of roses. So pretty that she stuns.

36. This teddy will be strong for you.


The barbells even have hearts. While he wears a medal for cuteness.

37. A country singer should always have her own guitar.


Trixie’s guitar matches her boots. While she dons a black dress and hat.

38. Say hello to Santa’s newest little helper.


Yes, he’s a Santa elf. Though he doesn’t sport pointy ears.

39. Lindsay always enjoys roasting marshmallows.


She’s dressed for the colder weather, too. Like the scarf and bow.

40. Guess it’s someone’s sleepy time.


He wears his own romper and bear slippers. Though he carries a rather mischievous expression.

41. Even among teddy bears, K-Pop is all the rage.


Well, it’s from Seoul’s teddy bear museum, what do you expect? Guess it’s “Oppa Gangnam Style.”

42. The city is always a bustling place.


This is from a teddy bear museum in Jeju. Yet, all the bears are in street clothes. One’s even checking her smartphone in the street.

43. Anyone in the mood for smores?


He has the graham crackers and chocolate. He wears an orange vest to be seen when going to the bathroom.

44. Ladies and gentlemen, the king.


Here’s bear Elvis in his white jumpsuit and red guitar. Yet, he won’t look so great in his Vegas years.

45. “Me, Pawzan. You, Jane.”


Here he swings with his jungle bear in harms. While the apes look on.

46. “Now let this be a fair fight.”


This can get ugly. But at least they’ll be stuffing leaking out by the end instead of blood.

47. Nobody surpasses this iconic bearsketball player.


This is supposed to be Michael Jordan during the 1990s by the way. He was the Lebron James of his day.

48. It’s always ice and snow in the polar regions.


Sure, polar bears and penguins don’t go together. But it’s a cute display nonetheless.

49. Must be hard to entertain 7 little bears.


This a display of Snow White and the Seven Dwarfs. Here she reads them a bedtime story in the woods.

50. Looks like we have the experts at work.


I think they’re supposed to be archaeologists. Since I saw a few bones and things.

51. Apparently, teddy bears have their own Jurassic Park.


And we come to some bears about to be eaten by a T-Rex. Don’t have much hope for them.

52. This bear has been through so many tissues.


This is a get well bear. Nonetheless, you have to love the pajamas.

53. Japanese bears dress in lavish kimonos.


Wonder if they’re supposed to be a bride and groom or an emperor and empress. Still, they’re adorable.

54. Nobody should miss the Winter Olympics.


I guess they’re watching some of the events. Includes snowboarding and cross country skiing.

55. Don’t think you can scratch this 7-year itch.


This is a teddy bear of Marilyn Monroe from The 7th Year Itch. Here her dress goes up from the air vents.

56. Bears always love their bread.


Here we come to teddy bears baking bread. The bears here also wear chef hats.

57. Everyone seems to love a royal wedding.


This one is of Prince Charles and Princess Diana. Let’s just say despite the fairy tale atmosphere, the marriage didn’t last.

58. These bears pay tribute to a Buddhist shrine.


Well, this is from a museum in South Korea. Got to love how the bears bow down to the Buddha.

59. Hera always looks like a queen.


She’s supposed to be the Greek goddess Hera, queen of Mount Olympus. Given that her husband can’t keep it in his pants, she’s got a very vicious streak.

60. Dionysus always knows how to party.


He’s the Greek god of wine and revelry. Still, his parties can get pretty wild.

61. These bears play on the beach.


A mother and daughter build a sandcastle. While a guy goes out surfing.

62. These bears have fallen on hard times.


This is a rendition of a famous painting. Indeed, they’re poor farmers. But it’s kind of cute.

63. Here the king consults with his advisers.


You can tell they’re his advisers due to their tall hats. From South Korea.

64. Seems like a leopard snuck in.


Okay, it’s a teddy bear in a leopard onesy. And it looks adorable in it.

65. This bear lady is rather enterprising.


She’s smartly dressed in a navy blue business suit. Like her scarf.

66. Seems like Gulliver is all tied up.


Here’s a teddy bear rendition of Gulliver’s Travels. Includes one giant bear and a bunch of little ones.

67. On Mount Olympus, Zeus is king.


Yes, that’s Mr. Sex Fiend with the Lightning Bolts himself. As he sits on his golden throne.

68. Beware of the ferocious Minotaur.


He’s supposed to be half-bear and half bull. And he’ll tear people to shreds with his cuteness.

69. This bear means business.


Yes, that teddy bear’s got a knife. So it’s best you stay away.

70. A small red dress can always stun.


This bear wears a sweet little red dress with a bow. Like her jewelry, too.

71. You’d think this was a rainbow bear.


This bear has bright colors all over it. So adorable and colorful.

72. This bear knows how to keep warm.


This is the female version of the Vermont bear. Comes with dog and blond hair.

73. Perhaps you’d want some candy from Lucy.


This is a Lucille Ball teddy bear. Please don’t employ her in any candy factory.

74. When you’re blue, make way for the cheerleading bear.


Comes with pom poms, flag, and megaphone. Like her bows. So adorable.

75. This teddy comes to support Team USA in the Olympics.


This was for the 2016 Summer Olympics in Rio. Nonetheless, he seems like quite the avid patriot.

76. This bear dresses in conversation hearts.


Well, it wears that sweater. Though they’re not making these chalk hearts this year.

77. Someone looks spiffy in a sailor outfit.


Well, this is for a little kid. Nonetheless, it’s a colorful get up with a pom pom hat. So cute.

78. This bear’s reading for 2.


Since she’s pregnant. As you can tell by her maternity dress.

79. Wonder if this is for a Korean wedding.


I guess it is, given the groom’s outfit. The bride wears a white dress.

80. No one can resist a bear on a rocking horse.


Indeed, the bear rocks a horse by the fire. So hard to resist. Awww.