Fashion trends come and go, but the internet is forever. Let’s take a stroll through the weirdest, most WTF fashion moments ever.
Did your favorite fashion faux pas make the cut? Share it in the comments!
22. That’s Not How Pants Work
It looks like she tried to pull an Urkel and hike her pants up to her armpits, only to have things go horribly wrong. At least she seems to regret her life choices as much as we regret having to look at this denim disaster.
21. Simba, Is That You?
Nothing out of the ordinary here. Just a leggy blonde model in a gold lamé dress with giant lions on her shoulders, walking a dog that also looks like a lion. Typical Saturday afternoon stuff.
Can you imagine wearing that coat in the summertime? You’d pass out from heatstroke after a block.
20. Jon Bon NO-vi
The early 90s were a different time…but not THAT different. Is the worst part of this the crunchy hair, the burgundy crushed velvet suit (with leather lapels!), or the sad little ribbon tie hanging from his collar?
Honestly, the worst thing might be that his suit clashes so badly with his wife’s purple Dynasty-style gown. Get it together, man!
19. I’m Your (Fallen) Angel
How did this happen? Why did this happen? We have so many questions—starting with where we can get one of these shirts. Celine Dion, Death Metal Goddess is the hero we need in these trying times.
18. White Meat Bieber
Spoiler alert: This won’t be the last time Justin Bieber appears on our list. Here, he’s sporting the finest faux fur throw blanket TJ Maxx has to offer. Guess Biebs needs his blankie.
17. You’re Not Fooling Anyone, Chet
There is so much wrong with this picture. It looks like Chet glue a Tribble to his head and stole the facial hair from a Civil War general. His shirt looks like a he’s wearing a blue bralette over a polo. Imagine your Tinder date walks in looking like this—what would you do?
There was a time when Paris Hilton was the most famous woman in the world. Love her or hate her, when she left the house, people talked about what she was wearing. As a trendsetter, she had the power to do great good…or great evil.
Unfortunately for us, she chose a sickeningly pink velour tracksuit from Juicy.
16. The OG Queen of Drama
Before there was Gaga, there was Cher. She wore this two-piece ensemble—you really can’t call it a “dress”—to the 1986 Oscars. She would go on to win a Best Supporting Actress statue two years later, but this was the Oscars appearance that has stuck in our collective imagination. She looks like the most glamorous Power Rangers villain ever.
14. An Unholy Union
In the collaboration that exactly zero people asked for, the makers of Tevas and Uggs decided to team up to find out if they could make the ugliest shoes on the planet. They did.
With the sole and straps from Teva sandals and the fur-lined fabric from Ugg boots, they managed to create something that will make your ankles sweat in the summer or your toes freeze in the winner. There is no good here. Only pain.
13. The New Addams Family
Do you remember that very strange period of time when Angelina Jolie dressed like Morticia Addams and gave us all very weird vibes about her relationship with her brother? Those were simpler times. She brought James Haven as her date to the Oscars in 2000, and although she still wears a lot of vaguely shapeless black sacks, at least she ditched the goth girl hair.
12. Who Wore It Better?
On your right, you’ll see reality star Kim Kardash—wait, no. Sorry about that. On your left you’ll see Kim, and on the right you’ll see a sack of oranges. It’s so hard to tell them apart. This fashion fail is but one of many from the Kardashian clan, who don’t care if they look good as long as people are looking.
11. Drop-Crotch Pants
Apparently Millennials looked at the terrible scourge of Hammer Pants from the ‘90s and said hold my beer! Dropped-crotch pants were a completely mystifying trend from a few years ago that has thankfully faded away. But we’ll always have pictures, so that someday our kids can laugh at us for wearing what looks like leggings and a baggy diaper.
10. Clear Vinyl Boots
Kanye has been trending in the news lately for a whole lot of reasons, but a few years ago, people were talking about his terrible fashion line. Kim stood by her man in the hideous clear boots he designed, but as you can see from the photo, no one looks good with their toes wrapped up like deli meat while their leg sweat steams the inside of their boots.