Trends aren’t constant.
This explains why people’s styles change over time. What’s cool before can’t be considered cool these days. Moreover, what’s trendy now may not be trendy in the next 5 to 10 years.
Although trends don’t last, pictures do. And unfortunately for people who considered themselves trendy before, their photos showing off their styles from years ago serve as reminders of their odd sense of style back then.
If you’re looking for something to make you laugh hard today, you’re in for a treat. Check out these 75 people and their worst fashion mistakes.
1. Opposite day
When everybody else wore black, white or something else, this guy chose to dress up as a girl for their school’s Opposite Day. Considering how he looked, the news went around quite quickly in his small hometown.
2. On MySpace
This is one good reason to be more careful about the photos you upload on social media. Keep in mind to upload only those photos you won’t feel embarrassed to see a few years from now.
3. Who’s that?
This guy wasn’t able to recognize himself in this picture. Well, who could blame the guy? He was only 16 years old when this picture was taken.
4. In a junior high year book
When this woman’s friend’s daughter found her picture in her old yearbook, she couldn’t stop laughing. The poor girl didn’t have a clue on what “cool” looks like back then.
5. What were they thinking?
Looking alike wasn’t enough for these twins. They had to make these customized shirts and cut their own hair
6. No regrets
Her mom told her that she would regret this photo. After 21 years, she’s still feeling great about it.
7. 12 years ago
These teenagers just had their baby when this picture was taken. There was no sign of regrets or sad feelings in this photo- just pure happiness.
8. Immortalizing the moment
The guy just defeated Guitar Hero on Expert. It was such a fulfilling moment that he felt the need to immortalize it in a photo. He was so overwhelmed that he didn’t think about putting on proper clothes.
9. Not what you think
No, this guy wasn’t going to a costume party. He was actually headed to his prom when he had this picture taken. (And yes, he didn’t have a date).
10. Like mother, like daughter
Mom was more of an 80’s goth/punk. She didn’t have problems supporting her daughter’s questionable phases.
11. The weird kid
This guy was aiming to get that weird kid vibes at school. He dressed up like this to look cool and mysterious. Fortunately, he got exactly what he wanted.
12. A Zumba baby
She’s too cute. She’s clearly giving off that 70s home aerobic workout vibes. She nailed the outfit!
13. An all-time favorite
This guy’s wife considers this photo as her favorite. Well, who could blame her? The guy looks pretty fora 20-year-old with pink hair.
14. Hard to guess
It’s hard to figure out this person’s age just by looking at this picture? Was he a 7-year-old boy or a 70-year-old grandma in this photo? We’ll never know.
15. A school photo
Cardigan? Turtleneck? Thick glasses? Although everything he’s wearing suggests that he’s a 60-year-old librarian, he’s actually just a regular kid posing for his school photo.
16. Before puberty
He was often picked on and bully. Fortunately, puberty was good on him and decided to give him a glow up.
17. This phase
This 14-year-old went through what she called the “Eminem phase”. It’s when you hang a hairbrush, pretend that it’s a microphone and rap your heart out.
18. Too cool
He spent most of his days watching The Matrix and Fight Club. He felt so cool after watching them that he had to wear two sunglasses.
19. A form of revenge
Despite the smile, this kid’s look was actually a form of revenge. His mom ended up crying after getting the picture.
20. The entire family
Being a family means supporting each other. That’s why these parents were more than happy to join their kid’s photoshoot with his chosen theme.
22. Too angry on a road trip
No, that’s not a 12-year-old boy. The kid standing next to the older guy was actually a 15-year-old girl who didn’t want to be involved in the family trip.
23. Fake photos
He used to stage photos like this and post them on social media for likes. This was around 2012 when Facebook was just starting to gain followers.
24. A weird hobby
These friends didn’t go to parties or socialize with other kids their age. Instead, they mimed and they were quite happy about it.
25. Halloween back then
This photo was taken in 1998. Apparently, back then, kids don’t dress up as sexy celebrities or cool rappers. They used to dress up like the Titanic and the famous iceberg that caused it to sink.
26. Looking good
Goggles? Tie? Belt? Bible? He’s out to impress the girls.
27. Like Whitney Houston
She thought that getting shorter hair and perming it would make her look like Whitney Houston. It was too late when she realized that it doesn’t work that way.
28. A different quinceañeras
Most girls her age would choose to wear sparkling pink gowns to celebrate the milestone. It was very brave of her to have an emo-themed celebration.
29. Pokemon birthday party
Contrary to what you might be thinking, this wasn’t the dog’s party. It was the boy’s birthday and he picked the Pokemon theme for the celebration. Fortunately, the dog had no objection.
30. A bit different
He wanted to look different and cool for prom so he wore a leather jacket instead. It’s probably one of the biggest mistakes in his life.
It’s hard to determine which made this post awful. Was it the caption? Was it the style? I’d say both.
32. When you’re an anime fan
She wanted to live in an anime that bad so she decided to make this. It’s not a bad idea, honestly.
33. Sisters, not lovers
They weren’t lesbians taking a “couple photo”. They were sisters proudly showing off the suits their aunt bought for them.
34. Sporting a fake wig
Your hair is your crowning glory. That’s probably the reason why this 13-year-old girl decided to wear a cheap wig to school.
35. Back in 2012
She probably had a hard time getting into the venue. She looked so exhausted in this photo.
He and his friends agreed to wear a plaid skirt for their school photo. He was the only one who showed up wearing it.
37. Feeling the style
He’s clearly feeling the style. He didn’t care if he ended up hurting others. The most important thing was that he felt cool wearing that style.
38. Dating in 2007
This photo just proves that looks don’t really matter. You can act goofy and wear an emo hairstyle and still find the love of your life.
39. In 8th grade
Notice the smirk? He was clearly proud of his style back when he was in 8th grade.
40. Early signs
His parents didn’t need to ask their kids if he’s gay or not. The signs were clear even at a very young age.