Creepy Vintage Halloween Photos

13 Creepy Pictures of Vintage Halloween Costume That Will Haunt Your Dreams

13 Creepy Vintage Halloween Costumes That Will Haunt Your Dreams

As the air grows crisp and the trees adorn themselves with shades of red and gold, Halloween enthusiasts eagerly anticipate the most nostalgic night of the year. Halloween has a rich history, and when it comes to costumes, vintage Halloween costumes hold a special allure. Let’s delve into the spooky past of why people have been donning costumes on Halloween for generations.

The origins of this tradition can be traced back to the ancient Celtic festival of Samhain. This celebration marked the end of the harvest season and the beginning of winter, a time when the veil between the living and the dead was believed to be at its thinnest. To protect themselves from wandering spirits, people in ancient times would disguise themselves in masks and costumes, laying the foundation for what would become the Halloween costume tradition.

In medieval Europe, the Christian church introduced All Saints’ Day (November 1st) and All Souls’ Day (November 2nd) to honor saints and the departed. These holy days preserved some Samhain customs, including “souling,” where people dressed in costumes and went door-to-door, singing and receiving food in exchange for prayers for the souls of the deceased.

Over time, the concept evolved. By the 19th century, Halloween had transformed into a community-centered holiday with parties and parades. People began dressing up as various creatures, witches, and characters, and the emphasis shifted from warding off spirits to celebrating creativity and imagination through costumes. How nice, right?

Well, let’s have a look at how some of the creativity and imagination from the past manifested in these pictures of vintage Halloween costumes. I tried to put them in order from least to most unsettling. Enjoy!

#1 The Pumpkin and the Blockhead

We will start with this nice little Photo. Cute huh? It probably was cute at the time but when it is translated to film, it takes on a whole other character.  The faded and scratched photo makes these vintage Halloween costumes look straight out of a horror film. 

Creepy Old Halloween Costumes

#2 Dead Horsemen... and Horses

I really have to give these people credit for getting their animals into the festivities. I hope the horses got a treat for their part. A skeleton costume is a classic, while the way it was done back in the day is just on another level of creepy from the modern take of this trope. 

#3 Creepy Lady Elaine and Wynn Butler

If you were on acid and decided to watch an old episode of Mr Rogers and then the Arcade Fire video for “Here Comes the Nigh Time”, this pair might incorporate into your trip. 

I don’t know about you but Lady Elaine haunted my dreams as s child and somehow this vintage Halloween costume manages an even more nightmarish appearance – even without the long nose.

#4 Going to a Dead Man's Party

Who could ask for more?… OK, I am showing my age with the Oingo Boingo reference here.

Those wonky skulls freak me out! 

#5 The Family of Scarecrows

If these guys were out in the corn field, it would keep out more than just crows.

#6 The Lollipop Kids From Hell

I don’t think we’re in Kansas anymore, Toto. These Lollipop kids have come for your soul… or maybe to kidnap Santa Claus. (That’s right, I mixed 2 movie references into this one.)

#7 Me and My Imaginary Friends

Simon was bullied at school so he dug into his necromancy book and got some backup. Now his assailants wake from their sleep biting their own tongues and pulling their hair.

#8 Waiting for the Night Train

#9 The Box Heads

It’s the masks that really give the creep-factor to these vintage Halloween costumes. I thought the large boxy head wrapped in trash bags were a nice touch.  Those sweaters are pretty cool though…

#10 The Council of Demons

I don’t know about you, but those mail carrier masks are just… yeesh!  Then there is a clown and a cop – two of the scariest things I can think of! 

#11 The Devil and The Gnomes

The Devil should have gnome better than to go out that Halloween. 

#12 BIG Teeth!

The freakishly large teeth make me uneasy (not that I am one to be too critical about teeth.) 

The mumified little corpse was a nice touch to go that extra mile in making this picture creepy. Is that a stick in its mouth? Let me know what you think in the comments.

None of this seems to be bothering the the Librarian from Sherwood Forest, however…

#13 The Hostage

While these vintage Halloween costumes on their own may not be the scariest, the boy in the picture makes this one the creepiest to me. The poor kid looks to be genuinely frightened. Maybe he was camera shy or maybe he was an unwilling victim.  OR, maybe the weird beard-thing brushing the back of his head was making him anxious. Who knows…

Bonus - The Mushrooms and the Gnome

This one is a bonus because I simply could not pass up these mushroom vintage Halloween costumes! While this picture is less creepy than the others, I just had to include the homage to the fungi. 

Ok, maybe the gnome guy in the front is pretty creepy after all…

The bus stops here. I hope you enjoyed this exploration of creepy old Halloween Costumes.

Drop a comment below to let me know which one you thought was the creepiest.

Maybe you might be inspired by the creativity of yesteryear and make your own creepy costume for Halloween this year. I think I might…

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