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.

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.

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.

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.

Looking alike wasn’t enough for these twins. They had to make these customized shirts and cut their own hair

Her mom told her that she would regret this photo. After 21 years, she’s still feeling great about it.

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.

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.

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).

Mom was more of an 80’s goth/punk. She didn’t have problems supporting her daughter’s questionable phases.

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.

She’s too cute. She’s clearly giving off that 70s home aerobic workout vibes. She nailed the outfit!

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.

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.

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.

He was often picked on and bully. Fortunately, puberty was good on him and decided to give him a glow up.

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.

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.

Despite the smile, this kid’s look was actually a form of revenge. His mom ended up crying after getting the picture.

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.

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.

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.

These friends didn’t go to parties or socialize with other kids their age. Instead, they mimed and they were quite happy about it.

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.

Goggles? Tie? Belt? Bible? He’s out to impress the girls.

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.

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.

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.

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.

She wanted to live in an anime that bad so she decided to make this. It’s not a bad idea, honestly.

They weren’t lesbians taking a “couple photo”. They were sisters proudly showing off the suits their aunt bought for them.

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.

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.

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.

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.

Notice the smirk? He was clearly proud of his style back when he was in 8th grade.

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.

The picture wasn’t photoshopped or edited. This was a real school card back in 2011.

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.

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.

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.

She wanted to look like Ludacris on her graduation. Unfortunately, she didn’t look anything like the artist.

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.

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.

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.

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.

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.

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.

She’s just 6 years old in this photo. She’s not a 40-year-old woman who does taxes for a living.

He was too happy when his mom allowed him to get the laser background. Not all kids were given that chance back then.

The parachute pants were such a hit back then. Even young kids were proud to wear them.

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.

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.

This boy’s class was asked to dress badly for the day. Considering his outfit, he clearly nailed it without much effort.

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.

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.

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.

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.

Her outfit was inspired by everything she adored back then. The Crow and Blade were just some of them.

This was how most teens looked like in the late 00’s. The glasses, big pants, and facial expression, this dude got everything right.

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.

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.

He almost didn’t fit the frame. The photographers had to zoom out just to accommodate his enormous hair.

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.

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.

He was trying to look cool for the pirate ship ride. He even tried dressing up like one.

Just looking at these girls, you’d know right away who they’re trying to look like. Unfortunately, they’re missing one member.

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.

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.

This teenager wore a fish costume and danced in front of an aquarium store. She considered it as her best job ever.

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.

Surprisingly, this boy looked great as Marie Antoinette. The hair and makeup looked good on him.