“Sexy Pennywise” and Other WTF Halloween Costumes

sexypennywise

Damn, do I love Halloween! The pumpkins, the candy, the decorations it’s all just good fun. But my favorite part are the Halloween costumes dressing up as someone or something else for a night is awesome. I used to be an actor so being a character for a night is my jam, it’s just in my DNA to love it. I love throwing costume parties, and I have managed to browbeat most of my friends into getting into the costume loving spirit with me each year.

I take my costume choices fairly seriously. Long gone are the days that I will buy some Plain Jane witch costume from the store and call it good. I may be a Basic Bitch in other ways, but not when it was comes to the all important Halloween outfit decisions. I like pop culture costumes, and being movie and television characters. I really like when other people put together fun costumes I would never think of, and every year I see some really creative ideas. Which is awesome.

Usually.

That being said, not all costume choices I have seen over the years have been “winners”. I have seen some pretty ridiculous, awkward, and baffling costumes and, while I give props to those who share my penchant for Halloween, there are some people who maybe need to dial it back a bit. Or dial it way, way up a bit. Or just not be a freak.

Behold, some of the weirdest and most loathed types of All Hallows Eve attire that I personally have witnessed:

The “What The Hell Are You Supposed To Be?” Costume

I see a dude standing at the bar one Halloween, wearing a blue body suit. He has a telephone cord wrapped haphazardly around his body, and a rubber chicken hanging from the cord. I’m stumped and keep staring, trying to figure it out. Accidentally make eye contact and oops, damn it- here he comes. Walking to our table with a big grin on his face.

“Ya tryin’ to figure out my costume?” he asks with a big, cheeky grin.

I give him a tight smile. “It’s a tricky one.” Which he did on purpose so that people would have to ask him all night, the big attention whore.

He was Chicken. Cord. On blue. Chicken Cordon Bleu.

He put his back into making an original costume; I’ll give him that. But was still dorky AF.

 

The “What The Hell Did You Think I Was Going To Think You Are?” Costume

One Halloween in college (this was the early aughts- an important detail), there was a heavy set gentleman with a bushy ginger beard, walking around the bar in a kilt, plaid sash, brougues, and carrying a set of bagpipes. The Austin Powers movies were huge at the time (early 2000’s, remember?) and here is this guy, in this outfit, on Halloween night, at a bar filled with people in various costumes. Riddle me this: Who would you think he was dressed up as that night? That’s right- Fat Bastard. He walks up to me, tugs on my tail (I was dressed as Catwoman) and says to me, “Who are you supposed to be? Catwoman?”

Well, duh- it was pretty obvious who the hell I was dressed as; gee, did the cat ears and mask give it away, dude? I turn around to say (with an eye roll) that yes, I was in fact Catwoman, when I see this guy has a great costume on! I mean, he was a dead ringer; way to win Halloween, man! With a smile, I poke him in the gut and say “I don’t have to ask who you are dressed as- you look awesome, Fat Bastard!”

Yeah.

No.

Puzzled, the man replies, “Um, I didn’t dress up for Halloween this year….”

Turns out, the guy wasn’t wearing a costume- this was just his “thing”. He just often wore traditional Scottish garb and played bag pipes at the bar. And I called him a fat bastard, right to his face. I said nothing (what the hell was I supposed to say to that?) and beat a hasty retreat, leaving my sister behind to awkwardly apologize because I’m a shitty sibling like that. (She still brings this up, over 10 years later- she told him I was just drunk. I probably was.)

 

The “Could You Have Possibly Put Any Less Effort Into It?” Costume

I once saw a group of girls at a costume party wearing totally normal, every day outfits and carrying small jars of various cooking spices (ya know, garlic, thyme, rosemary, etc.) All just so they could pose for pictures holding up these jars, smiling like they are just the most clever girls to ever walk the Earth.  What exactly was their “costume”?

The Spice Girls.

Ugh.

Don’t. Ok? Just….don’t.

 

The “Your Mother Must Be So Proud” Costume

Picture this: A girl, wearing the shortest dress I’ve ever seen in my life. A small trash can is tied around her waist with the letters C-U-M written in Sharpie on the front.

Anyone?

Yep, you guessed it! She was a “Cum Dumpster.”

Way to keep it classy, sweetheart.

 

The “I Hope You Get Your Ass Kicked Later” Costume

Some jackass was wandering around my friend’s Halloween party one night, covered in fake blood with women’s high heels attached to his clothes. I didn’t know (and really didn’t care) what the hell he was he was supposed to be, but he made sure to keep standing next to me, messing with the shoes on his costume, practically itching for me to ask. Just so he would go away, I finally took the bait.

“And you are supposed to be….what exactly?” I ask.

He leans in, all close and creepy, and says, “I’m a Lady Killer.”

I should have punched him in the face.

But he wasn’t even the worst one at this particular bash! Oh no, that honor goes to the asshole that wore a stethoscope around his neck and kept handing out lollipops to girls. He took (way too much) pride in announcing to everyone at the party that he was dressed as a “Pediatric Gynecologist”.  Because psychos are all around us, ladies and gents. All around us.

 

The “Way To Make Light Of A Tragedy!” Costume

I’ve seen so many of these costumes over the years. A few “honorable” mentions….

Adolf Hitler: Because the Holocaust was just such a hoot!

Jeffrey Dahmer: This guy wore a prison jumpsuit and rigged a broom handle to his ass crack, and walked around all night eating gummy candy made into the shape of body parts.

Charles Manson: Complete with the swastika tattoo on his forehead and carrying a copy of Helter Skelter. Nothing says “party” like remembering how innocent people were murdered back in the Age of Aquarius, amirite?

Siegfried and Bloody, Tiger-Attacked Roy: Ok, fine- this one made me chuckle a bit but still…..

 

The “I’m A Sexy (Insert Regular Costume Here)” Costume

I think it’s safe to say this is a phenomenon we are all aware of- Halloween as an excuse to dress like a hooker. We’ve all seen it, some of you (ahem, ok, us) have even done it.  Why be just a witch when you can be a sexy witch? Why be a regular ol’ police officer when you can be a sexy police officer? Or why be anything at all when you can just slap on some lingerie and cat ears and call it a day? It’s not a concept I’m bothered by but it’s gotten over the top, yeah?

One of the most eye roll-y ones I’ve seen is the “Sexy Nun” costume; um, why? It makes me feel weird because I feel like it plays into some odd fetish stemming from Catholic school or something, and I don’t want to think about that on Halloween. Or, ya know, ever. Bonus (I guess?) to the chick who took it further by being a “Sexy PREGNANT Nun”.

And as I recently saw, making a cameo Halloween 2017: “Sexy Pennywise”. If you’ve lived under a rock for the past couple of months and actually don’t know (but, how?), Stephen King’s “It” got a movie reboot. The starring monster of that story is an entity that takes many forms, but most notably as a clown called “Pennywise”. Much like the Wu Tang Clan, Pennywise ain’t nothin’ to fuck with; he is a child murdering evil bastard that gave me nightmares as a child- and I don’t think I’m alone in that. So of course I knew Pennywise was going to popping up everywhere this Halloween- what I didn’t expect was a slutty, female version. Because apparently Pennywise wasn’t giving people enough of a tingle in the nethers. I would argue that’s a good thing. But for the truly sick among us, child slayers just got a whole lot sexier.

Fantastic.

 

Well, I hope you enjoyed my version of the Ghosts of Shitty Halloween Costumes Past. What awful/ridiculous/genius/etc. costumes have you seen over the years? Hit me up in the comments because I really love new Halloween costume ideas. Despite some definitely cringeworthy get-ups over the years, costume parties will always be the reason I love this holiday. Cheers to those who go the extra mile- your dedication to the cause makes me smile. Unless it’s an homage to a child pedophile/killer; then I reserve the right to spit in your drink.

Just kidding! (Or am I?……)

Happy Halloween!

Festively Yours,

Sam

xoxo

 

 

 

One thought on ““Sexy Pennywise” and Other WTF Halloween Costumes

  1. Ha ha love this. One year, in college I literally dressed as a hooker. I had said I was going to be Hannah Montana and bought a wig, but the wig made me look like a hooker, so one of my friends suggested I just be a hooker, and I decided okay.

    I put bruises on my arms with makeup and had a friend who went as my pimp with a cane. It was more of a social commentary about how we glorify the objectification of women.

    And who the hell would think it would be funny to go as Adolph Hitler?

    Like

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