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The Scariest Halloween Costumes of All Time

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From the creepy homemade masks worn by trick or treaters of yesteryear to the horrifying Halloween costumes of the 1800’s we take a look at the scariest Halloween costumes of all time.

The origins of Halloween are somewhat uncertain. Many people believe that some of the traditions associated with this holiday originated from ancient harvest festivals, in particular the Gaelic festival, Samhain, the festival that marked the end of the harvest period and the beginning of winter. While others believe that Halloween began solely as a Christian holiday, independent of the ancient pagan festivals.

Today, Halloween is celebrated in many countries especially the US, where big business has cashed in on the commercialization of this popular holiday.

Vintage Halloween costumes - The Scariest Halloween Costumes of All Time

However, this hasn’t always been the case. Dressing up has long been associated with Halloween and it’s believed that it was originally done to ward off evil spirits. When people wanted to dress up for Halloween celebrations they had to rely on the materials that were available to them at the time. Not only that but each costume was also heavily dependent on the wearer’s own crafting skills.

As these photos prove, the end result was often far more terrifying than any of them probably intended.

Two men dressed in devil costumes holding a young boy - The Scariest Halloween Costumes of All Time

Some of the makeshift costumes that people made were so scary that they appeared to genuinely frighten those that saw them. The young boy in this photo looks absolutely terrified to be posing with the two in the black demon masks.

Vintage monster Halloween costumes - The Scariest Halloween Costumes of All Time

By the mid 1800’s, photography was becoming increasingly popular. It was also becoming more affordable and people started taking photos to capture the important moments in their lives.

The photographs that they took, now allow us to look back in time and see some of the truly creepy Halloween costumes that people once wore.

Scary old Halloween costume - The Scariest Halloween Costumes of All Time

It seems that the older the image is the more creepy the subject looks. While the costume in this picture is definitely unsettling on its own,  the grainy quality and faded edges of the photo lend an extra uncertainty to the the scene.

The contrast of the black and white makes the figure’s costume difficult to make out with any deal of clarity except for the two large, white eyes. The fact too, that the photo appears to have been taken on a cold winter’s day with snow on the ground and bare, leafless trees lining the empty street all adds to the photo’s mystique. It looks like it could easily be a scene straight out of a horror movie!

Old Halloween costumes - The Scariest Halloween Costumes of All Time

The poor manufacturing processes of the time and the fact that many of the costumes were hand made makes the masks that the people are wearing in these photos look bent and out of shape and some even appear to be melting. These imperfections give the figures a horrifying appearance.

Three children dressed in Halloween costumes - The Scariest Halloween Costumes of All Time

People made their own costumes from whatever they could get their hands on. Masks were often simple moldings with little detail that made the wearer’s face look expressionless and cold.

A group of women dressed up for Halloween - The Scariest Halloween Costumes of All Time

Some costumes that may look totally bizarre today, were often modeled on popular traditions of the time. This photo shows five women dressed as dead bodies in a manner that was once used to photograph the deceased.

A mosquito Halloween costume - The Scariest Halloween Costumes of All Time

People had to be creative. This photo shows just how scary a homemade Halloween costume can actually be.

Imagine seeing this thing coming towards you while taking an evening stroll!

As bikes of the time didn’t have reflectors, it may have appeared as if a gigantic mosquito-like creature was actually flying towards you!

Two boys dressed in scary Halloween costumes - The Scariest Halloween Costumes of All Time

Because there was no mass produced Halloween costumes available it meant that everybody’s look was unique. There were no Scream masks or Freddy Krueger gloves and no scary movies for inspiration or reference. The ideas and concepts of each costume came from the creator’s mind and reflected the things that they found scary.

Not knowing who or what the person is actually supposed to be enhances the viewer’s feelings of uneasiness. Imagine running into these two while out trick or treating late on Halloween night?! The costumes not only hide their identities but also their intentions.

Vintage clown Halloween costumes - The Scariest Halloween Costumes of All Time

When this photo was taken, clowns were still known as the lovable clumsy misfits of the circus and were not thought of as evil or sinister in any way. Today, thanks to Stephen King’s It, the sight of a clown is enough to send many people running in fear.

It is very likely that the people posing for this photo had no idea that dressing as their favorite circus characters would end up creating such a terrifying picture years later!

Scary Halloween Costumes - The Scariest Halloween Costumes of All Time

Even the people in this photo probably had innocent intentions, yet today this picture embodies many things that we find scary. The grainy quality of the photo. The old paintings on the walls. Even the smiles of the people posing add an extra uneasiness. It would not be surprising to learn that the moment after this photo was taken, the woman on the left’s head did a full 360 degree rotation!

A woman dressed in a doll Halloween costume - The Scariest Halloween Costumes of All Time

Dolls were also a popular choice for Halloween costumes. Similar to those that dressed as clowns, people who wore doll costumes were probably not doing it to look intentionally scary. The concept of a creepy, murderous doll only came about after the release of the 1988 horror film, Child’s Play.

The most uneasy thing about this photo is the fact that the woman has a more lifeless face than the doll that she is carrying.

A group photo of people dressed in Halloween costumes - The Scariest Halloween Costumes of All Time

Dressing up as animals seemed to be popular too. As well as wearing over-sized characterization masks of other people.

Old black and white photos of large groups of oddly dressed people always seem to give off a creepy vibe. Is it that the characters all appear to be staring right at the viewer or is it the uncomfortable feeling of not knowing who any of the people are hidden beneath the costumes?

The fact that there is also a single boy not wearing a mask at all places questions in the viewer’s mind. Why is he the only one in the photo without a mask?

A couple dressed in badger Halloween costumes - The Scariest Halloween Costumes of All Time

People may have had plenty of creativity but often didn’t have the ability to make the costume just as they had imagined it. That lead to some very warped and rather horrifying creations.

This photo shows a couple dressed as animals, possibly badgers. Ironically, while their masks may not look exactly as they intended them to, the couple actually look far scarier than if they had intentionally dressed as a ghost or vampire.

Disney Halloween costumes - The Scariest Halloween Costumes of All Time

As the characters created by the Walt Disney Studio gained popularity in the 1920’s and 30’s, children began to dress as their favorite characters for Halloween. This photo that shows several Disney characters holding hands in front of a flaming car has become rather well known across the internet.

What makes this image unsettling to the viewer is the way that the grins on the characters masks tend to suggest that it was them that set fire to the car.

While the exact origin of this photo is unclear, it certainly does leave you with an uneasy feeling – the happy smiling faces of the wholesome Disney characters juxtaposed with the chaos of the flaming car behind them.

Giant eyeball Halloween costumes - The Scariest Halloween Costumes of All Time

By the mid 20th century, science fiction movies were becoming popular. As a result, more people began modelling their Halloween costumes off the aliens and other-worldly beings that they saw in these films.

The sci-fi movies that were being made at the time were considered to be B grade films and the costumes and props that were used were not first rate. As Halloween party goers began to copy these designs, there were some very strange and often terrifying costumes conceived.

Vintage witch Halloween costume - The Scariest Halloween Costumes of All Time

Iconic figures like ghosts, witches, skeletons and demons were all popular costume choices with each incorporating the creators own personal touch and flair. Many of these classic horror characters are still around today.

As several popular stories and tales about these creepy characters were written long ago, it may be possible that our unconscious mind associates these older images more closely with these stories.

Halloween urban legend photo - The Scariest Halloween Costumes of All Time

Recently, some of these old Halloween photographs have become associated with urban legends and creepypastas. This image was supposedly taken in 1962 and shows a black, hooded figure posing in a group photo. The story goes that the hooded man attended a Halloween costume party where he locked all the doors to the house and killed seven of the party goers before fleeing the scene. He was never caught but the mask was allegedly found in 1969 and is currently in the custody of the FBI.

While many believe the story to be true, its origins are difficult to verify. The story has become popular more recently thanks to it spreading through social media. Whether or not this black and white photo is actually linked to the case is unclear.

Looking at the image however, its not difficult to believe that the story may be true. The alleged killer looks oddly out of place even in a room of people dressed in costume and it’s certainly not a stretch to assume that this was the last photo taken before he committed his sinister act.

Creepy Halloween costumes - The Scariest Halloween Costumes of All Time

The reason that these vintage Halloween costumes appear to be scarier today is most likely a combination of many factors. The grainy, out of focus photography. The bizarre and imperfect masks that hide the people’s faces and the fact that the images themselves show unfamiliar places and people from long ago. While most of the people seen in these photos have already left this world, these images are all that remain as clues about who these people really were.

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