At the time, these Halloween costumes were hilarious, clever, maybe even “edgy.” Fast-forward a few years… and wow. Just… wow. Whether it was a DIY disaster, a culturally clueless choice, or something that now requires a public apology and a lawyer, these outfits did not stand the test of time. They were the kind of costumes that got laughs back then and side-eyes today. And let’s be honest: some of us have photos that we pray never resurface (but you know they will).
So here it is: a look back at Halloween costumes that aged like unrefrigerated deviled eggs. From “politically incorrect” to “fashion crimes punishable by jail,” we’re dragging these skeletons out of the closet, literally.
Don’t worry, we’re judging ourselves, too. If you ever wore a pun costume involving a trash bag and a bad attitude… yeah, we saw you.
1
A Fake Creepy Man is Grabbing Her From Behind
Halloween or a PSA about personal space?
2
“Gingerbread Man”: Literally a Ginger Covered in Bread
This pun hurt more than it helped.
3
This Homer Simpson Costume is Scary for All the Wrong Reasons
Somewhere between uncanny valley and sleep paralysis demon.
4
“Cool Whip” and “Neigh-Neigh”: A Joke That Shouldn’t Work
When puns, props, and horse heads unite… it’s weirdly iconic.
5
“Adam Sandler or a Lesbian?”
Bold of her to ask what we’re all thinking.
6
“Sick of the H0ez”, In a Hospital Gown
High school edginess meets… mild misogyny.
7
A Child. Dressed as a Pack of Cigarettes.
Nothing like a bit of childhood and lung disease, wrapped in cardboard.
8
Costume: "Party Girls Who Always Get Pregnant"
Offensive? Yes. Problematic? Also yes. Regret? Most likely.
9
Teen Dressed as a Burnt-Out Mom with Babies
The most realistic costume of all time. Send coffee.
10
Giant Red Lips and a Bag Full of Babies
This one… has layers. None of them okay.
11
Another Paper Bag Kid… Now It’s a Trend?
Just say you gave up without saying it out loud.
12
Grocery Bag Girl: She Contains Multitudes
Organic? Biodegradable? Emotionally unwell? Yes.
13
Paper Bag Boy: Budget? Check. Shame? Also check.
This is peak “I forgot it was Halloween.”
14
Together They Form…
You know what’s scarier than Halloween? Public commitment to this idea.
15
This Kid is Dressed Like He’s Pooping Mid-Halloween
Some costumes are scary. This one is just… disturbing.
16
Pretending to Get Blown Away by Wind
Umbrella inside-out, hair flying, full commitment. Oscar-worthy.
17
Toddler Dressed as a 30-Year-Old Gamer Addict
Pringles, dark circles, and zero will to live. Childhood goals?
18
Man Dressed as “Life”… Hands Out Lemons
Deep. Poetic. Kinda passive-aggressive.
19
Twister… But Make It Inappropriate
Why is the red dot THERE? Who approved this?!
20
Two Kids. One Giant Shirt. Infinite Regret.
Because nothing says friendship like forced proximity and mild suffocation.
21
“Error 404: Costume Not Found”
The universal sign of “I didn’t try and I want you to know it.”
22
Classic Ghost Sheet, But Somehow Still Terrifying (or Cringe)
It's giving “last-minute,” it’s giving “don’t make eye contact.”
23
They Made Their Daughter a Literal Trash Can
This costume throws away self-esteem AND subtlety.
24
Newspaper Dress, Breaking News: “Fashion Crimes on the Rise”
Extra! Extra! Read all about how this made it out the door!
25
Cereal Killer Dad Joke Come to Life
Frosted Flakes meets felonies. A spoonful of regret included.
26
They Dressed Their Kid as Hannibal Lecter. The Kid Is Not Okay.
Nothing screams “fun childhood memory” like simulated psychological torture.
27
Couple’s Costume: Divorce Court Energy
He’s the grumpy housewife. She’s the trucker husband. Love is… confusing.
28
Trapped Inside a Giant Foot in a Flip-Flop
Somewhere in there is a human… probably questioning every decision that led here.
