13 Iconic Vintage Costumes To Recreate This Halloween

It's time for cold-weather, candy, and pumpkins, but nothing says Halloween like a good costume. Stroll with us down memory lane as we reminisce about just how terrifying vintage dress-up could get back in the day!

By: Maggie Miller

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Of all the holidays, the atmosphere surrounding Halloween may be the most unique. The entire month of October is one frenzied buildup to a night that celebrates the collision of festivity and fear. Though the past century saw a gradual transition from pagan-based, homespun disguises to more contemporary sources of inspiration, all of these vintage costumes unequivocally put the fright into Halloween night.

1955, Young Cowboy & Pumpkin Man

This ca. 1955 photo pairs a less-than friendly looking jack-o-lantern mask and a very wary young cowboy. It feels very classic Halloween for the time coupling America's fascination with Westerns and painted pumpkins.

1905, Ghostly Ms. Frizzle

Unbelievably, this horrifying photo was not taken on the set of the next Purge installment, but at a rural schoolhouse. An adult, perhaps a teacher, stands behind a lunch table set with Halloween crafts and decorations. Early on in the century, costumes tended to have more serious overtones, connecting with early pagan and Christian traditions that were “deeply linked to ghosts and superstitions”. This teacher’s dedication to the horror theme put Ms. Frizzle’s wardrobe to shame.

1910, Masked Woman

A masked woman on roller skates sounds like the plot for a superhero origin story, but this mask would probably send her fan base running. Costumes from the early 1900s were often made at home, with whatever materials were available. This handmade disguise’s overly large eyes are all the more unsettling thanks to the addition of a delicate lace veil. Imagine trick-or-treating and spotting this visage racing toward you at unnatural speeds. No thank you.

1923, Two Witches

By the 1920s and ’30s, adults and children were attending Halloween “masquerades” and costumes began to see more of a pop culture influence. It was during this time that companies began producing pre-made costumes for purchase. Factory-made or not, the Wicked Witch of the West looks like a beauty queen next to the over-exaggerated features of this crone mask.

1925, Ghost Trio

Despite the availability of readymade costumes, many during the 1920s still opted for a handmade approach, to terrifying effect. This trio of ghost children makes the masked villains from The Strangers look downright neighborly. And let’s not even get started on their devilish candy buckets.

1930’s, Little Girl with Halloween Décor

To be fair, this girl’s costume is relatively tame. What really sparks dread are the haunting expressions of the inanimate objects surrounding her. I’m not sure who thought a deranged clown, dead-eyed Mickey, rage monster pumpkin, and cat with eyes popping out of its head were child-friendly photo props, but whoever it was would excel in the horror industry.

1931, The Coven and the Hare

It’s hard to say what exactly is going on in this picture from a Wabash, CA playground, but it looks sinister. Three children dressed as witches lean toward a crouching nightmare beast, perhaps attempting to banish the paper abomination before it can scar more children. The flat-faced bunny monster is made all the more disturbing by the cloth bag that covers it’s (hopefully) human head. How does it breathe? Dark magic.

1948, Boy in a Clown Mask

As the century wore on, Halloween pranks grew more extreme, perhaps in part because of the emboldening effects of costumes. In response, law enforcement and national officials took steps to rebrand the holiday as a child-centric celebration. Unfortunately, it appears elected officials missed the memo that homicidal clown masks are arguably one of the more horrifying plagues to childhood.

1955, Girl Wearing Paper Halloween Mask

It could be the atmospheric greyscale of the photo or the eerily empty classroom that makes this costume so deeply unnerving. Then again, it could also be the featureless paper mask resting atop a small child’s shoulders. This arts and craft project gets an A+ for craftsmanship and dread.

1960, Four Masked Marauders and A Jack O’ Lantern

While the ’60s signaled a general shift away from masked merriment for older party-goers, masks still found footing among younger trick-or-treaters. Illuminated from below by the sole light of a Jack O’ Lantern, this foursome looks ready to conjure a specter from the darkest recess of night.

1978, Gore Galore

By the late ’70s and early 80’s much of the superstitious overtones that had informed costume design had fallen to the wayside. However, with the advent of gory “splatter-horror”, terror still found a way to permeate Halloween fashion. Imagine a street filled with pint-sized variations of this grotesque visage. That’s not traumatic for anyone, right?

1978, Pickle Man

This small child’s Halloween memories will forever be tainted by images of the petrifying pickle mutant and his masked accomplice. Between the fleshy nodules covering its body and the painted face emerging from the crumpled flesh of a gargantuan pickle, this costume combo is truly the stuff of nightmares.

1985, The “Friendly” Ghost

There really is nothing more “vintage Halloween” than a sheet with holes cut into it. Probably because its the most emotionally scarring costume known to mankind. Nothing spells doom like a mask that abscures all features save for two shadowy eyes. Cue the Slenderman music. Side note: the rope around the neck seems particularly inadvisable and menacing.

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13 Iconic Vintage Costumes To Recreate This Halloween

Related To:

Shop This Look

1955, Young Cowboy & Pumpkin Man

1905, Ghostly Ms. Frizzle

1910, Masked Woman

1923, Two Witches

1925, Ghost Trio

1930’s, Little Girl with Halloween Décor

1931, The Coven and the Hare

1948, Boy in a Clown Mask

1955, Girl Wearing Paper Halloween Mask

1960, Four Masked Marauders and A Jack O’ Lantern

1978, Gore Galore

1978, Pickle Man

1985, The “Friendly” Ghost

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