20 Vintage Photos of Halloween That Are Slightly Creepy

  • Oops!
    Something went wrong.
    Please try again later.
·3 min read
In this article:
  • Oops!
    Something went wrong.
    Please try again later.

Today, one can simply turn to the internet to find scary movies to stream or creepy costumes to wear. But our modern versions of spooky and kooky fail to elicit the same feelings of unease that the scares of decades or centuries ago do. So, to get you in the true Halloween spirit, we conjured up some old-school photos of celebrations from Halloweens past. There's something so unsettling about black and white images of folks who are long gone, with their pillowcase masks and deadpan gazes. It's almost as if you're locking eyes with bona fide ghosts! So, without further ado, here are 20 vintage Halloween photos with just the right amount of spookiness to satisfy that itch for a scare.


This creepy pumpkin mannequin

It feels like this photo was snapped just moments before this jack-o'-lantern destroyed everything in the house.


This masked man

Man in a ski mask for halloween vintage halloween photos
Man in a ski mask for halloween vintage halloween photos

All this man did was add gloves and a mask to his daily outfit and voilà, he's terrifying.


These ghoulish gents

Is anyone else getting Clockwork Orange vibes from the gentleman in the front on the right?


This eerie yearbook photo

This photo, courtesy of the 1921 East Texas State Normal College yearbook, is eerily reminiscent of the final shot in The Shining.


This group of NOPE

The longer you stare at this vintage photo, the more horrific it becomes.


This masked old lady

Wearing a "sad old lady" costume to a children's Halloween party is a bold choice in 1939. We understand why those little ones in the background look so uneasy!


This man and his dummy

This smug, big-headed dummy makes Chucky look like child's play!


These forest creatures

This 1918 photo is one part Wes Anderson film and one part fever dream.


This unflappable Frankenstein's monster

This man's poker face and refusal to break character make this 1950s snapshot deeply unsettling.


This nightmarish 1946 Halloween parade

Once upon a Halloween, this gigantic man-faced scarecrow rolled down the streets of Anaheim, California—and he definitely gave kids nightmares.


This wrestler you don't want to mess with

This wrestler is giving The Undertaker some eerie competition.


This spooky styling

Wacky makeup and a crazy 'do make for a frightening fashion don't!


This toothy pumpkin

Why does this jack-o'-lantern need so many human-looking teeth?!


This frightening family portrait

Could these three be any creepier? We're not even sure if the one in the middle is human!


This confusing cracked egg costume

How do you even go trick-or-treating in a costume without arm holes?


This evil pumpkin party

Jack-o'-lanterns were evidently all the rage at the University of Southern California in 1890.


This bewitching woman

The shadows, the skull, the smoking cauldron—this costume and photo may be spooky, but at least she nailed it!


This Halloween onesie

This adult Halloween onesie sported by actress Mary Miles Minter in 1921 is, at the very least, a fashion faux pas.


This masked bandit

This woman's toothy grin and mask-covered eyes make her 1928 costume feel more sinister than silly.


This spirit with unfinished business

This stereoscope is proof that even back in 1889, people enjoyed the thrill of a manufactured scare. And for more spooky entertainment, Here's the Most Famous Ghost Story in Your State.

To discover more amazing secrets about living your best life, click here to follow us on Instagram!