Take A Trip Down The Rabbit Hole With These Creepy Vintage Halloween Costumes

By October 17, 2013


Okay, stick with me here as I have something I need to explain. The other day as I was just canoodling around on the internet as one does when they are procrastinating and not owning up to the millions of tasks they need to accomplish, I found myself on Pinterest, of all places. Now, I’m still not completely sold on this site since it kills my attention span almost immediately.

However, I found a board with a bunch of odd images and upon clicking a link, I was sent down one of those rabbit holes (hence the scary bunny above) that exist online that ended up taking roughly two hours out of my day. That’s right, I got lost in the crazy and exciting world of vintage Halloween pictures. I’ll admit right here and now that I am not the first to post a blog featuring the images I’m about to share with you but it just seems like the perfect time and place to do so.

Enough talk, let’s turn back the clock (I’m a rapper)!


I’ve been known to listen to a lot of creepy sounding old timey music. Hell, Tom Waits does that style quite well. However, it’s folks like these above that make me afraid of children. Especially those children who live in the barn and make masks out of burlap sacks and your dead skin. Take all of my candy and money….and the soul of my first born! Gah!


For those of you unaware, I grew up with little means. Many of my costumes growing up were cheap store bought items or something I threw together from hand me downs that were…uh….handed down. I give this kid credit as it’s obvious he had a similar childhood. I mean, this is one fantastic Bob’s Big Boy Transvestite Zombie costume he has going on! First place in my book!


My assumption here is that the three pictured above were caught in the midst of celebrating another lovely Christmas in…Bavaria or wherever. What better way to party than to dress up as the evil Krampus and then take little unsuspecting Hans on a lovely trip through the snowy maze of pine trees out back? I’m so sorry, Hans.


What the hell is going on here? Are these cheap ass scarecrows or are there really people under those bag headed mask thingies? Apparently even back in the 20s, high top fades were all the rage. Yeah, I got nothing.


If this were a game of Pictionary, my guesses would be: Michelin Men, Sausage People, and Fat Inflatable Mummies. But it’s not Pictionary, and I’m a bit clueless as to what’s going on here – and I also think way too much about tires, sausages and fat mummies.


For some reason, I’m thinking this gentleman in “fancy dress” above is a distant relative to Ron Swanson. Because, Ron Swanson is real! HE EXISTS!


Dawww! Look at the happy baby. What a happy baby! Too bad the baby is unaware he is the perfect creepy unicorn snack. For all creepy unicorn in retro suits munch on babies like they’re jerky…because to unicorns, they are!


What the hell am I looking at here? Oh I know! The dude from Duck Dynasty and one of the members of Jabbawockeez caught a fetish bear with the intention of making the greatest viral video of all time. Am I right? What do I win?!


This hell beast is about to eat this little girl. Don’t make eye contact. Just move along. Nothing to see here.


I’m just going to go ahead and assume that this picture was taken before Hitler’s rise to power. And if it was, how unfortunate for this gal dressed up in her weird…clown…costume? And if it wasn’t before Hitler’s Germany, well then…what a stupid costume! STUPID STUPID STUPID!


Go find another restroom, ladies. This one is forever occupied.


What I think happened here was this couple had been invited to a costume party and waited until the very last minute to figure out what to wear. Finally, the husband had a fit of genius, grabbed the rotary phone and wrapped it around his head. His loyal wife followed suit. And together they made a family of phone-headed children who grew up to live a reclusive life in today’s society. I blame Apple.


Sometimes I feel like somebody’s watching me!


All your wildest dreams and worst nightmares have been realized. Giant mosquitoes have become self aware and are now riding bicycles. Hide your wives, hide your kids!


An evil clown, crazy witch, minstrel cop, two minstrel slave wench zombies and Pocahontas all walk into a bar…


It was a busy day when The Sawyer Family gathered together for the portrait above to be taken. The sun was already about to set and there was still so much work to be done. Who else was going to render the meat and complete their recipe for the annual Texas/Oklahoma Chili Cook Off?


And tonight we’re gonna party like it’s 1929!


I have a sneaking suspicion here that this photo would have been more creepy without the mask. Someone get the skipper here a scotch, pronto!


It’s nice to know true love knows no bounds. Even if that applies to people with Muppet rat heads. Seriously Rizzo, do you happen to know what’s going on here?


Quit your crying, Bat Boy! Show and tell is now over! As they say, misery loves company. Thanks for appeasing my misery, folks! Now, why not give back to the community by sharing your favorite creepy Halloween pics in the comments below, or passing this article along to your friends? That’s only fair, right?


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Aside from throwing words onto your screen here, he has written for the likes of FEARnet, Examiner, Dread Central and MTV Movies Blog. And yes, he was Percy on VR Troopers.