20 Vintage Photos of Halloween That Are Slightly Creepy

Homemade costumes were far more terrifying in the 19th century.

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

State Archives of Florida/Florida Memory/Alamy

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
Kirn Vintage Stock / Alamy Stock Photo

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

These ghoulish gents

Vintage Images/Alamy

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

This eerie yearbook photo

Public Domain/Northeast Texas Digital Collections

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

Kirn Vintage Stock/Alamy

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

This masked old lady

Library of Congress

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

Matthew Corrigan/Alamy

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

These forest creatures

Public Domain

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

This unflappable Frankenstein's monster

Kirn Vintage Stock/Alamy

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

This nightmarish 1946 Halloween parade

CC BY 2.0/Photo courtesy County of Orange

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

Everett Collection/Alamy

This wrestler is giving The Undertaker some eerie competition.

This spooky styling

Everett Collection/Shutterstock

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

This toothy pumpkin

Everett Collection/Shutterstock

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

This frightening family portrait

Everett Collection Historical/Alamy

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

This confusing cracked egg costume

Everett Collection/Shutterstock

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

This evil pumpkin party

Public Domain/USC Digital Library

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

This bewitching woman

Everett Collection/Shutterstock

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

This Halloween onesie

Public Domain/Exhibitors Herald

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

This masked bandit

Public Domain

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

This spirit with unfinished business

Everett Collection Historical/Alamy

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.

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