The Dark Scary World of Vintage Halloween Costumes (Third Edition)

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Whether intended to be scary or cute, many of these vintage Halloween costumes seem rather terrifying for some reason. Perhaps they made costumes differently. Or maybe it’s the photography since black and white can make things look significantly scarier than color. Maybe they were just more creative. But whatever the reason Halloween back then apparently seemed much creepier than today’s equivalents. And if you lived back then, chances are you’d probably wouldn’t want to run into any partiers or trick or treaters. Nevertheless, for your reading pleasure, I give you yet another installment of some really creepy old Halloween costumes to send a shiver up your spine.

  1. You might want to beware of the clowns living in Uncanny Lane.

By the way, do you know Pennywise the Clown from It? Well, these are his parents. Or grandparents. I’m not exactly sure.

2. Perhaps you can be a deer and what the hell is that thing?

Then again, the deer head costume kind of looks a bit creepy as well. But it’s nothing compared to the one kind of resembling a badly designed ghost cat.

3. For a devil costume all you need is a dress and matching horns.

Sure they may not look scary. Yet, the hooked tails kind of look out of place.

4. Think of this classroom scene as Arthur meets Pet Semetary.

Man, those masks are so creepy as hell. Guaranteed to give you nightmares for weeks.

5. Oh, look two trick or treaters.

Okay, you can take all the candy you want! Just go away and don’t kill me!

6. Children always look forward to a Halloween parade.

Might want to flee the neighborhood when they’re around. Unless you have a huge stock of candy.

7. Apparently, Spock goes for purple haired chicks.

Actually that doesn’t look like Spock at all. Besides, couldn’t the parents just use make up and pointed ears? Seems less scary.

8. Please don’t look behind the bushes.

Because these two girls will straight up murder you. Sure they might be playing around. But piss them off, you’ll soon regret it.

9. This boy is quite a skilled bear baiter.

For one, this costume pair makes light of cruelty to animals. Second, that is the most terrifying bear I’ve ever seen. Please don’t sick that thing on me.

10. Be wary around anything with a big head.

After all, the one with the bag was never seen again after this picture was taken. Sure the big headed guy might look silly but avoid if you value you life.

11. Beware of the scary ghouls with flashlights.

Yes, they’re trick or treaters. But give them anything with razor blades and they’ll put you through hell.

12. You’ll surely be endeared with this clown wearing musical cats.

On second thought, those cats are terrifying. If there’s a cat version of Deliverance, I bet any money they’d be in it.

13. On Halloween, best not to piss off this wicked witch.

No, she’s not the kind of witch you’d see on Harry Potter. And if you do anything stupid, she can easily turn you into a toad.

14. “Smile for the camera, children!”

We have idea what happened to the kid in the cap after this. For he was never seen again.

15. Keep away from those wearing large masks.

Yes, those are incredibly horrifying. So is the cat. Might want to avoid if you value your life.

16. Try getting these women out of these large bottles.

They’re dressed as gin and port. And from how the labels are placed, I’m not sure if they’re wearing much else.

17. Someone in this picture has their mask on upside down.

But the mask is nevertheless terrifying just the same. Also, you don’t want to piss off those at the fountain.

18. When these two clowns visit your neighborhood, you better be on your guard.

Make sure you have plenty of candy. For if you don’t, chances are you’ll never be seen again.

19. Better give this devil his due.

Yes, that mask is certainly menacing. So you better give him candy before he takes your soul.

20. Sometimes a so-called cute creature can be upright murderous.

Yes, the costumes here are kind of scary. But the panda and chipmunk are truly the stuff of nightmares.

21. No, you don’t want to shake hands with the pumpkin man.

At first I thought it was a Halloween decoration. Still, I don’t think this girl’s exercising good judgement.

22. Whatever you do, it would be wise not to crash this party.

For all you know, party crashers could be on the menu. So you might as well stay away if you value your life.

23. When trick or treating, kids, there are just some homes you must stay away from.

This house would fall among those you should skip. Doesn’t matter if their candy is good. Because they could easily put you in a pot or a hot oven.

24. Of course, many costume parties should always have a group photo.

Yet, you best not want to see these people in a dark alley. Or intoxicated. Also, what’s party hat Hitler doing here? Talk about terrifying.

25. Don’t want to know who let these dogs out.

For all I know, they’d drag me into the woods and murder me. So best you keep away from these two.

26. Perhaps you might want to pay a visit to the pumpkin man.

May not be as scary as Donald Trump. But the pumpkin head and abdomen is unsettling. Still, have to admire the squash wagon.

27. This guy just wants someone to sit with him.

Though better if you shouldn’t. For you never know what he might do to you. Then again, he might be just lonely.

28. On Halloween, sometimes you might want to know what happened to certain kids’ heads.

I know it’s a mask head. But that just doesn’t look right for some reason. Not sure why.

29. I’m sure this girl wouldn’t want to hold hands with this Uncle Sam.

Even the old costumes not meant to be scary are terrifying. This especially goes for ones of Uncle Sam for some reason. Yes, I feel for that girl, too.

30. Even ghosts can get tired sometimes.

But that’s still a very creepy costume. Also the one with the black leather mask is quite menacing.

31. Sometimes it helps if your costumes match.

Though stripes don’t detract from the horrifying expressions. Best to keep away if you value your life.

32. On Halloween, chances are you might run into a ghost in your neighborhood.

But if you run into this one, try to get out of sight before they haunt your dreams. Otherwise, nobody will see you again.

33. When Dracula and Frankenstein band together, no one is safe.

Sure they’re store bought masks. But they nevertheless seem scary as hell.

34. Keep away from the clown in the corner.

Yes, clowns can terrify us. But this is especially so in black and white photography.

35. Even a pumpkin from bags can horrifying onlookers.

That face may have a smile. But you don’t want to mess with them. Seriously, don’t.

36. Somehow I’m not sure what’s going on with this rabbit.

Cute little bunny rabbit in an outfit isn’t what I have in mind with this one. In fact, wouldn’t be surprised if this girl took out an ax.

37. If you thought the twins from The Shining were creepy…

Those masks are just uncanny and menacing. Guaranteed to give you nightmares.

38. Sometimes it helps of you crack a few egg…people.

This woman’s costume doesn’t even have arm’s for God’s sake. Yet, she doesn’t seem to mind. Not sure why.

39. There’s a strong chance you might be visited by green people from another world.

If they visit you, best to give them what they want. Else, they might vaporize you.

40. Pennywise the Clown has nothing on this guy.

Hell, this guy makes Pennywise look like a clown at a birthday party. Why he doesn’t get the Stephen King treatment, no one knows.

41. Sometimes a costume might seem scarier under candle light.

You can see this in action with this ugly vampire. I’m sure he’d give the guy from Nosferatu a run for his money.

42. Even a wolf can seem scary near a jack-o-lantern.

Not sure if he’ll kill your grandma or blow down your house. But if go near him, you probably don’t want to know.

43. There are some trick or treaters you simply just can’t greet.

Just throw candy at them and have them leave. But not those Dum Dum lollipops. Or candy corn. Else, you’ll regret it.

44. Guess this is what you’d call a 1930s insane clown posse.

Okay, they might not be juggalos. But they’re dressed as clowns. And they’re certainly insane.

45. Only a clown can enjoy a slow dance with a ghoulish ghost.

Though which one I should feel bad for is a difficult question. After all, both seem likely to kill you in your sleep.

46. When these 3 ghosts visit the neighborhood, it’s time to run.

Because if you don’t give them candy, they will haunt your dreams. Or perhaps worse.

47. A jolly clown like this boy is one to avoid.

After all, he might get his jollies from hacking people to pieces. Don’t believe me? Just look at his face.

48. When ghost drive by night, be very afraid.

Still, if you drive near these, you might want to give them the right of way. Because you might regret it if you don’t.

49. Don’t worry about these witches hanging.

Though the old crone seems like one who’d use a candy house to eat children. The other woman doesn’t seem to mind.

50. You can create a scary costume with a white sheet.

Yes, these are certainly menacing. Definitely guaranteed to haunt your dreams.

51. No, you don’t want to touch that clown’s nose.

Though the other kids seem pretty terrifying as well. Nevertheless, best to avoid them on the street.

52. When you see some ghastly folks in cone hats, it’s time to run.

Best not to push their buttons. For you don’t want to be chopped to pieces. So don’t piss them off.

53. Sometimes a simple paper bag can make all the difference.

Must take an artist to make a simple brown paper bag inspire nightmares. Stephen King would be proud.

54. When you’re on a budget, go with newspaper.

Not sure what he’s supposed to be. But at least he’s willing to get creative. Yet, he’s a long shot in any costume contest.

55. Better not look behind you when bobbing for apples.

Because if you do, these undead will kidnap you and bury you alive. So happy apple bobbing, kids.

56. Introducing for one night only, the Skeleton Triplets.

You should really see them dance since they’re such a scream. Also inspire screams when looking into their stone cold faces.

57. When you see this witch around, her little brother won’t be far behind.

So please treat them well and give them candy. But not candy corn since they will absolutely murder you if you do.

58. Even the Devil can be trusted around babies.

Okay, I know this is a picture of siblings. But that masks might suggest the boy’s less than a wholesome influence.

59. Here’s a photo of Pennywise from his childhood.

Let’s just say this was one kid in the neighborhood you didn’t mess with. Because he’d basically kill you.

60. On Halloween, best not mess with these witches.

After all, to these girls, black magic is serious business. And if they turn you into a toad, consider yourself lucky.

61. When he shows up, it’s your time to go.

Since he’s the Grim Reaper. Okay, he’s dressed up as one. But he’s quite frightening.

62. You might want to watch your back with these little devils around.

If you think they’re scary now. Just imagine them with their masks on.

63. Children always enjoy community trick or treating.

But you’d almost mistake this bunch for a horde of horrid monsters. Avoid them like the plague.

64. Apparently, these clowns have taken a couple of hostages.

And it’s likely these two boys may not have long to live. Poor angels.

65. Now this kid has a rather funny looking face.

Never underestimate the power of paper mache. And yes, this mask is terrifying.

66. The difference between these two is in black and white.

No, these two aren’t the aliens from “Let That Be Your Last Battlefield.” Because they didn’t have Star Trek at the time.

67. Bet you wouldn’t want to run into these trick-or-treaters.

Seems like you’ll find plenty of scary masks here. So best to either give them candy or avoid.

68. Don’t look now but Frankenstein’s monster is in the neighborhood.

Though to be fair, Frankenstein’s monster isn’t supposed to be bad. Rather it’s Dr. Frankenstein who’s the real monster.

69. You never know what you can make with paper bags and yarn.

And yes, they’re certainly frightening. Talk about creepy craft projects.

70. Thought Anne Jetson didn’t resemble a horror movie character.

Yet, this one makes a cartoon character seem like she’s from an uncanny valley. Eeek!

71. Should you attend this Halloween party, best to leave as soon as you can.

And yes, I can feel for the guy without a costume in this. Chances are, he won’t be coming home that night.

72. Not sure if he’s a soldier or executioner.

On the other hand, the woman’s dress goes perfect with the wallpaper. Though I wouldn’t mess with the guy with the ax.

73. You’d swear these women’s hair would stand on end.

And they all seem tucked into a sheet like they’re standing. Indeed, I don’t understand it.

74. Apparently, Nathan Bedford Forrest Elementary School wasn’t known for its sensitivity training program.

There’s a reason why we don’t want people to use a cone hat on their ghost costume. Because it brings a startling resemblance to what some white supremacists wear.

75. Dead Mickey Mouse and Batgirl Thing say goodbye.

And yes, their costumes seem to defy all explanation. Yet, they’re also incredibly terrifying.

76. Hope you never run into this rare bird.

Because she doesn’t seem very friendly. Also wears high-heeled shoes.

77. Sometimes you can do plenty with a cardboard mask.

Sure it’s a very cheap Halloween costume. But at the same time, it turns a child into a neighborhood psychokiller.

78. Seems like demonic monsters revel in the great outdoors.

Though you wouldn’t want to be out when they’re in the neighborhood. And yes, I hear they do kill unsuspecting bystanders.

79. Everyone always has fun at the skeleton dance.

But they sure don’t give any bones about freaking out the neighbors. Or anyone else.

80. Sometimes the scary is all kept in the family.

And let’s just say they always dress for dinner. But yes, the women will certainly give you the heebie jeebies.

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