20 of the Biggest Fashion Fails in History

Over the years, there have been numerous fashion fails that have left people cringing. Happy pants, mud jean vests, and shoulder pads are some of the worst fashion trends that were once popular. These days crocs with socks and tight jeans have become fashion no-nos. But of all these fashion fails, there are some that should never be repeated.

These trends, many endorsed by celebrities, often inspire fans and followers to adopt them. But like a supermodel tripping on the runway, these fashion fails fall flat. While it’s essential to express yourself through fashion, also understand it is important to make sure your choices are both stylish and tasteful. Below is a selection of the biggest fashion fails in history that need to be avoided. 

20 of the Biggest Fashion Fails in History

1. Jean Thong

Rumor has it Justin Timberlake and Britney Spears wore jean thongs under their iconic matching denim outfits they rocked at the 2001 American Music Awards. That should be reason enough to highlight how horrible this fashion trend was. 

2. Mud Jean Vest

Apparently, the missing piece to having the perfect expensive jeans vest is looking like you just rolled in a puddle of mud. 

3. Mickey Mouse Is in the House

Mickey Mouse is a beloved cartoon character. He’s a legend that changed the industry forever. Like a classic Mickey Mouse cartoon, this fashion fail is stuck between a rock and a hard place. 

4. Eyes in the Back of Your Behind

Look deeply into the eyes of this fashion disaster. When they look at you, it’s like you’re the only person in the room. Whatever you do, don’t break eye contact or you’ll miss the full moon. 

5. Barley There Jeans

The barely there jeans are ideal for any celebrity looking to cause a stir and make headlines when showing up on the red carpet for the Oscars, Grammys, or Emmy Awards. On the other hand, this type of outfit is considered normal for the Met Gala. 

6. Mud Stained Clothes

It appears that mud-stained clothes are all the rage these days. Perhaps celebs like Katy Perry and Ariana Grande will one day wear mud-stained dresses to match their mud-stained shoes on a red carpet. Well, we hope that’s mud! 

7. Anxiety for Kids

Anxiety for Kids clothing line has the right idea. Kids will grow up to become adults full of anxiety and worry; they might as well start them young. From the same brand comes Depression for Teens and Stress for Adults. 

8. So Fine Jeans

So Fine jeans take denim to a whole new level. Anyone who wore these cheeky jeans would be committing the fashion faux pas of the century. Well, unless it’s Kim Kardashian or Harry Styles. They could pull it off. Maybe Queen Elizabeth II when she was alive? 

9. One Toe Show

Celebs like Kylie Jenner, Doja Cat, and Helena Bonham Carter walk the red carpet in stylish outfits, but none would ever be seen dead wearing these toe exposoing shoes. This fashion disaster is hard to put into words and something we are glad is not a modern trend. 

10. Pizza Shirt

Some fashion fails are more confusing than others. Most people love pizza, but there are a few foodies who can’t stand the delightful Italian treat. According to these pajamas, some people hate pizza so much they want to fight it. These pajamas are so confusing it is impossible to tell if it’s a fashion failure or promoting a pizza fight club. 

11. Elf Girl Swimming Shorts for Men

Excuse me; my eyes are down here. It takes a bold person to wear these swimming shorts featuring an imge of a little girl elf right where the crotch is. They’re so bold you might need to do a background check on whoever is wearing them. 

12. Teaching the Kids About the Solar System

Clothing companies have a responsibility to help educate children about the solar system. This company accurately displays Neptune and Saturn while also makring the locatino of (Ur)anus. 

13. Red Spot

Portugal has produced some of history’s greatest footballers. If there’s one thing they know, it’s soccer and fashion. The team’s unique shorts feature an oddly placed red dot, giving their rivals something to aim for. It brings a new meaning to “where the sun doesn’t shine.” 

14. Crabby Flip Flops

At first glance, these crab flip-flops are fashion failures. Most people would never wear these to the beach let alone around the house. If there’s one celebrity we think could pull them off it would be Pete Davidson. He’d somehow manage to walk down the red carpet and leave with the most beautiful woman at the event. 

15. Bear Jacket

Celebrities often wear the most outrageous and stunning outfits they can find when attending award shows. Some stars show up wearing black from head to toe, like Kim Kardashian, while others come dressed as food, like Lady Gaga’s famous meat dress. It’s that rare time Hollywood celebs are encouraged to let their creativity flow. That said, the golden bear jacket is atrocious and a fashion faux pas to most people.

16. Will Ferrell’s Crotch

Will Ferrell is one of the most famous actors and comedians in Hollywood. He rose to fame as a cast member on Saturday Night Live and became a household name starring in the Christmas classic Elf. Fans of the movie were thrilled to buy Elf socks featuring Ferrell. The socks also show off Ferrell’s best feature and most extraordinary talent, his crotch. 

17. Coffee Stained Shirt

There are some days when everything that can go wrong will go wrong. You have a big job interview the same day your car breaks down, you miss the bus, and then you spill coffee all over yourself. It’s easily the worst morning of your life. Well, it turns out that fashion is going in that direction. Now you don’t have to wait for a bad day to look like you had a bad day. All it takes is throwing on your coffee-stained shirt and everyone will think things are going south. 

18. Bad Grammar

It’s rare that a piece of clothing is both a fashion failure and offers confusing advice. There is nothing that young girls in this world can’t do. They can become sports icons like Serena Williams or a media mogul like Oprah Winfrey. As this t-shirt encourages: “girls is can the therefore.” In other words, girls can do anything, unlike this tee that needs a spell and grammar check. 

19. Giving Up Is an Option

Sometimes a piece of clothing just speaks to a person. There are hundreds of t-shirts sporting positive affirmations like “Impossible is Nothing,” “Protect this House, and “Just Do It.” Well, finally, a fashion blunder had resulted in a t-shirt made for quitters. “Yes, giving up is simply an option.” So is being a poor sport, taking your ball and going home, and claiming you didn’t lose is all good according to this t-shirt. 

20. Mustard Dress

Apparently, a brilliant designer was once in the middle of a wild food fight. They were trying to hide when they got hit with a bottle of mustard. As they stood there covered in mustard, they had an “aha” moment. Why not an entire clothing line covered in food?

Despite being a terrible idea, someone designed this stunning dress with stains to look like mustard. We’ve heard they’re working on a ketchup summer dress, a relish mini-skirt, and hot dog bun speedos for men.