25 Totally Odd & Awesome Vintage Halloween Photos

Halloween = Creepy

Halloween is a time for ghosts, goblins, and kids in costumes that range from cute to creepy. It’s a day ripe for remembering, especially in photographic form.  When you look back at older Halloween photographs, the first thing you notice is how much creepier they are than today’s snapshots. Be it a store bought costume or something lovingly made by mom, these figures in these photographs go from frightening to just plain freaky. And in all their oddness, there is something beautiful and eerie, something that really represents the Halloween spirit.

Check out this collection of 25 odd, awesome, and interesting photographs of Halloween from eons ago.

  • Just Masks 1 of 25
    Really, all they need are the masks to make these costumes creepy. They don't need black gowns or wacky clothes, the masks do all the work.
    Photo Source: Halloween Forum
  • Roar? 2 of 25
    This kid is looking all sorts of creepy with this lion mask which is paired, for some reason, with a jumper and a hat. That outfit is really what brings the creepy.
    Photo Source: City Rag
  • Witch With a Bike 3 of 25
    Forget the broom, this witch travels by bike, with a broom attached, 'natch.
    Source: Primary Primitives
  • Popeye & Pals 4 of 25
    Now this is the creepiest Popeye mask I've ever seen. And he has some creepy pals like the Uncle Sam, the skeleton and the little boy who's just wearing black, with friends like this, he doesn't need to dress up too much.
    Source: MinuteManWife
  • Double the Creepy 5 of 25
    Not one creepy kid but two creepy kids. Those masks really are disturbing.
    Photo Source: Haunted Air via Time
  • Ghostly Ghost 6 of 25
    It's not just that this person is dressed up as a ghost that makes it creepy, but that the image is so faded and muted that the ghost seems, well, ghostly.
    Photo Source: All Hallows Design
  • Lovely Ladies 7 of 25
    Their stance is just like they're posing for a flirty pic, but the creepy masks totally change the message.
    Photo Source: All Hallows Design
  • Kid & Dog 8 of 25
    I love this photo. A child and their dog both dressed up as clowns. And they are both so perfectly posed and still.
    Photo Source: CityRag
  • Halloween Parade 9 of 25
    It's a Halloween Parade, old school style. The second kid is my favorite.
    Source: 13 Visions
  • I Don’t Know Either 10 of 25
    Look at these costumes. Can you figure out what they are supposed to be? My closest guesses would be a hillbilly space guy, a robot boxer, Mr. Pants Head, a human jockey and a soldier/butcher.
    Source: Bogley
  • Who is This? 11 of 25
    Is it a ghost? A bunny? A ghost bunny? So confusing and creepy.
    Photo Source: Trocadero
  • Hold Hands 12 of 25
    A little boy and a little girl hold hands in front of a house, and creepiness ensues.
    Source: Via Buzzfeed
  • Adults in Costume 13 of 25
    Some of these kids have been pretty darn creepy, but this gaggle of ghoulish adults have taken creepy to a whole 'nother level.
    Photo Source: Haunted Air via Time
  • Big Baby 14 of 25
    An adult dressed as a baby is always creepy, but the look and feel of this one is so awesomely odd.
    Photo Source: Haunted Air via Time
  • Fortune Tellers 15 of 25
    A lion, a witch and a duck walked into a fortune teller's tent and...well, you're going to have to make up your own punchline for this one.
    Photo Source: Haunted Air via Time
  • Witches 16 of 25
    What I love about these are just how classic the witches are. They've got the hats, the robes, the brooms, crooked nose, warts and all.
    Photo Source: Etsy
  • Way Spooky 17 of 25
    If I opened my door and saw this being looking back at me, well I'd run the other way.
    Source: 13 Visions
  • Even Spookier 18 of 25
    I thought the last photograph was creepy, but it just got creepier. This one is so wrong.
    Source: 13 Visions
  • Meet the Devil 19 of 25
    Here he is. The devil. In kid form.
    Photo Source: Graves and Ghouls
  • Group Shot 20 of 25
    Love all the vintage store bought costumes. And I'm struck by the simple buckets a couple of the kids are using, not something you see very often these days.
    Photo Source: THe Duquesne Hunky
  • A Little Leg 21 of 25
    One of these lasses showed off a little leg while her little friend gave her best zombie pose.
    Photo Source: CityRag
  • American Indian 22 of 25
    There was a time when there wasn't any kind of PC issue with dressing up as an American Indian for Halloween, now it's not as popular. I think the oddness of this outfit is an example of why.
    Photo Source: All Hallows Design
  • Devils on a Fence 23 of 25
    Not one, not two but four little devils were spotted sitting on a fence. Time to run the other way.
    Source: 13 Visions
  • Old School Masks 24 of 25
    There is something so creepy about these simple old school masks, even creepier than a Scream mask or a Freddy Kruger mask of today
    Source: MinuteMansWife
  • A Boy & His Pumpkin 25 of 25
    Yes, do not mess with a boy and his pumpkin.
    Photo Source: Haunted Air via Time

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Article Posted 6 years Ago

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