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.
21.
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.
31. Cringe-worthy
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.
36. Tricked
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.
41. Real or not?
The picture wasn’t photoshopped or edited. This was a real school card back in 2011.
42. The complete outfit
Back then, people don’t mix and match outfits and accessories that much. They prefer to use the same color for everything just like this kid.
43. Copy+paste
The woman on the left had her eyes closed when the photo was taken. For some reason, the photographer felt it was right to crop her eyes from a different photo and paste them over this one.
44. A Q-tip for Halloween
Back then, being anything you want for Halloween wasn’t that complicated. You can be a Q-tip and no one will judge you for that.
45. Like her favorite artist
She wanted to look like Ludacris on her graduation. Unfortunately, she didn’t look anything like the artist.
46. Being cool in the early 2000s
It wasn’t Halloween when this photo was taken. It was just a random day. The guy decided to take the photo and make the background using MS Paint.
47. First day of school
She looked so happy on her first day as an exchange student. Looking back, she’s not so sure what to feel about the photo anymore. What was wrong? She was torn between her socks and her haircut.
48. On the second date
Most people think that second dates are about candle-lit dinners and fancy restaurants. Well, that’s not always the case. Back then, second dates meant chilling at home.
49. Before a concert
This boy was out to see Linkin Park and Korn. Obviously, wearing the right outfit was a must. Taking someone with you to the concert was also necessary. In this case, he was out with his mom.
50. Looking grumpy
Being a punk wasn’t easy for this guy. Every time he needed to go out, he had to make sure his hair was perfect and that he’s wearing all of his accessories.
51. Like Patrick Swayze
This guy aimed to look like Patrick Swayze when he got the mullet and permed his hair. Unfortunately, he ended up looking nothing like the American actor.
52. Too young to be too old
She’s just 6 years old in this photo. She’s not a 40-year-old woman who does taxes for a living.
53. Circa 1991
He was too happy when his mom allowed him to get the laser background. Not all kids were given that chance back then.
54. Those days
The parachute pants were such a hit back then. Even young kids were proud to wear them.
55. Black and pink
There’s a lot going on with this girl’s outfit. She was wearing stripes, checkered print, mesh, and boots all at the same thing. It was a good thing she’s wearing that beautiful smile. It tied everything together.
56. Clueless
This guy had no idea what happened to him in 6th grade that made him look like this. Well, considering how he was looking, he should probably just quit trying to figure that one out.
57. Effortless
This boy’s class was asked to dress badly for the day. Considering his outfit, he clearly nailed it without much effort.
58. Mission accomplished
She wanted to make a statement so she showed up to a university wearing this. It didn’t take a long time for her to complete her mission.
59. Odd pair of stockings
At first, you’d think that there’s nothing wrong with this woman’s outfit. However, when you take a closer look at her leggings, you’d notice something odd. Yes, she was wearing fishnets stuffed with grass.
60. Showing off her tan lines
At her school, tan lines were considered as a status symbol. When she went out to get hers, she decided that her face was the perfect spot to have them. For sure, other students noticed them right away.
61. Going to a senior prom
Got no tuxedo for the prom? Don’t worry. You can just wear a tuxedo shirt and be on your way. Just remember to avoid taking photos. You’ll just end up regretting it.
62. Everything she liked
Her outfit was inspired by everything she adored back then. The Crow and Blade were just some of them.
63. Typical 00’s teen
This was how most teens looked like in the late 00’s. The glasses, big pants, and facial expression, this dude got everything right.
64. The new employee
This photo was taken on the day he was hired. It was only right that he posed this way. He deserved it for getting the job.
65. A mistake that lasted 2 years.
This kid went through a “Harry Potter phase” for 2 years. With the hair and the glasses, there’s no need to explain what the phase meant.
66. The ‘fro
He almost didn’t fit the frame. The photographers had to zoom out just to accommodate his enormous hair.
67. Those eyebrows
Eyebrows are supposed to look like sisters and not twins. However, for this girl, it looked like her eyebrows had a huge fight before picture day.
68. The look of embarassment
When her mom told her to smile for the camera, she frowned in an instant. Well, it’s hard not to see why. Her hair’s not the best that day.
69. At Disneyland
He was trying to look cool for the pirate ship ride. He even tried dressing up like one.
70. These girls
Just looking at these girls, you’d know right away who they’re trying to look like. Unfortunately, they’re missing one member.
71. Not the last airbender
This guy didn’t mention why he got this haircut. The only thing he could say about this photo was that it was taken for his junior yearbook. He expressed no regret or shame for wearing this haircut that day.
72. Warning
This photo serves as a warning to not try tequila and have your picture taken the very next day, particularly if it’s your first time trying the drink. Your photo will end up haunting you for years.
73. The best job
This teenager wore a fish costume and danced in front of an aquarium store. She considered it as her best job ever.
74. An odd choice
He wanted to look like a cowboy. Although he looked great, it’s still not clear where he got the inspiration from. He didn’t live on a farm. He didn’t even have cows near his place.
75. Cosplay at age 8
Surprisingly, this boy looked great as Marie Antoinette. The hair and makeup looked good on him.
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