Embarrassing Pictures Of Teens Back Then Look Nothing Like The Teens Of Today

By Media Feed | Published

If you’ve ever browsed TikTok even once, you’ll have noticed that it’s nearly impossible to tell a 15-year-old from a 20-year-old there thanks to their impressively put-together looks, makeup skills, and deft camera work.

None of us looked anywhere near as good—we sported awkward glasses, braces, and as much color in our outfits as possible. Here’s proof.

When Fashion Was About Comfort

woman wearing propeller hat at the pier
Photo Credit: JaimeeLou32 / Reddit

Before the era of crop tops, TikToks, soft girls, Eboys, and whatever the kids are calling themselves these days, 15-year-olds like this one had no problem sporting a propeller hat with a hint of emo on Mackinac Island.

The Karate Kid Re-Imagined

School photo of girl in karate gear holding kamas
Photo Credit: casswie / Reddit

Teens today may not even be aware that the Karate Kid didn’t start with Jaden Smith. This girl was ahead of her time and showed girls could do it just as well. Her only downfall was her choice of background, which she proudly picked herself.

Tie-Dye Is Life

tie dye outfit in front of garage
Photo Credit: PRAISEninJAH / Reddit

This was the first day of school in junior year. He confirmed that even his boxers were also tie-dye. The good news is that tie-dye is currently making a comeback in fashion, so he’s actually still on trend.

A Young Lost Soul

dramatic black and white picture of sad girl in mall bathroom
Photo Credit: ItsOkImNotALady / Reddit

Look at her face. She looks like she’s leading a very difficult life and really struggling to pull through in the mall bathroom. It looks like shopping therapy wasn’t paying off that day.

Is This Real Life?

posing in matrix outfit
Photo Credit: denob / Reddit

The answer in this case is no. This is the Matrix, or at least a Matrix-inspired outfit that this kid insisted would be a good idea to wear to school. Little did he know it just looks like he raided his mother’s closet.

“Business On The Top, Party On The Sides”

dude with mullet wearing a tux
Photo Credit: F1HdN / Reddit

Why commit to just one hairstyle when you can get away with having two? Leave it down and you look like you’re ready for a good time. Put it up and you look like…well, that’s open for interpretation.

No Need For A Holiday To Dress Up

man sitting on sidewalk dressed like sexy vampire
Photo Credit: deleted / Reddit

This young man loved to dress like a vampire. To clarify, this was his everyday look and not a costume for Halloween. He looks like he could write some really good dark poetry at a hipster open mic.

Embracing The Ginger Life

guy with ginger hair, ginger car, ginger clothes
Photo Credit: deleted / Reddit

Some people with ginger hair find it hard to fit in as they stand out with their orange hair. This young man had tons of confidence and decided to take the ginger to the next level by completely embracing it in everything he did.

In A Hurry To Grow Up

bald man with high school stuff
Photo Credit: DesmondDHume / Reddit

He shaved the middle of his head and dressed up as an old man in high school. It’s still unclear why teens are in such a rush to grow up, but specifically why a bald, middle-aged man with terrible fashion was this kid’s standard for what it meant to be an adult.

The More The Better

girl with coloful outfit and plenty of plastic accessories
Photo Credit: paneradfisk / Reddit

Forget that less is more. Back in the day more was more. Even if there was a slight risk that you might plank forward at any second from the weight of the thirty plastic necklaces on your neck.

There Was A Vision

medieval time picture with young girl
Photo Credit: deleted / Reddit

She actually begged her parents for this picture. This is the kind of picture you show to your children when they don’t understand why you’re denying their requests. You’re just trying to prevent their embarrassment.

How Many Bangs Can You Count?

girl with bangs and clips
Photo Credit: jadejong / Reddit

The answer looks like it’s exactly six strands of bangs. This is exactly why they warn against cutting your own bangs. Is that really going to stop you in your rebellious years, though?

The Family Who Shares Awful Haircuts Together

family mushroom mullet haircut
Photo Credit: deleted / Reddit

In 1988, this family decided that it would be a great idea for everyone to get the same haircut and then even went to commemorate with photo evidence. There is never going to be a one-style-fits-all haircut for the whole family. Ever.

Lookin Dapper

man in blue suit
Photo Credit: BeepBoopWhat / Reddit

At 15, he was given the honor of being the best man, an honor he could only live up to by matching a skinny bow tie with a matching cummerbund.

“Thought I Looked Like some ’70s Folk Singer”

70s singer man
Photo Credit: garybuttville / Reddit

It’s unclear what is worse here, that creepy smile or the mushroom-meets-mullet haircut that he thought made him look like a ’70s folk singer. Let’s hope he’s gotten a haircut since.

A Refreshing Matching Outfit

watermelon suit button up and shorts
Photo Credit: Tankerton81 / Reddit

This 1990s full-on watermelon walking shorts and matching button-up shirt outfit is another example of fashion that has found its way back. If it returned, then it couldn’t have been that bad in the first place…right?

It’s A Vibe

kid in fedora hat sitting in fancy lobby
Photo Credit: leadpie / Reddit

You know how sometimes you look like a kid and you feel like it’s a full-grown man trapped in a much younger body? This young man doesn’t look like someone you want to mess with.

“Me In The Late ’80s… So Edgy”

POSING ON TINY BENCH in purple buttonup
Photo Credit: juggling-buddha / Reddit

It’s hard to tell if he’s really tall or if for some reason they made really tiny benches in the ’80s… Maybe they started having to make bigger benches to accommodate the growing fast-food industry and its consumers.

A Country Boy At Heart

young boy in cowboy hat
Photo Credit: paintballpmd / Reddit

You’d think this young man’s outfit is a simple reflection of his country lifestyle, except he lived nowhere near cows or a farm. Perhaps he just wanted to embody the hardworking characteristics of a farmer.

It’s Not A Hobby, It’s A Lifestyle

posing with all his pokemon in bed
Photo Credit: mutakii / Reddit

“I asked my mom to take a picture of me with all my Pokémon.” Except, she looks like a proud mom posing with her kids on their first day of school.

When it came to Pokémon, you either completely embraced it as a lifestyle or you had nothing to do with it.

The Best Of Both Worlds

blonde bangs with brown hair
Photo Credit: barista91 / Reddit

This is what happens when you have a blonde mohawk, cut the rest of the hair off, but still insist on keeping the bangs. This must be the origin of ombré hairdos.

New Year, Same You

girl wearing miss adorable hello kitty t-shirt, tiara, stockings and SpongeBob belt
Photo Credit: CinnamonDruid / Reddit

She thought she was the coolest kid at the party, and can you blame “miss Adorable”? You can’t exactly argue with someone who wears a tiara paired with a SpongeBob belt. That’s basically royalty.

The Reason Behind Bad Eyesight

watching tv too close at computer desk
Photo Credit: butthuffer696 / Reddit

“Back when I badly needed corrective lenses and couldn’t be more than six inches from any TV.” You’ll find that a lot of us wear glasses today for this reason.

Also shoutout to the classic Cosmo and Wanda.

He Was A Skater Boy

skaterboy poses with car
Photo Credit: Randall_Butternubs_ / Reddit

If Avril Lavigne’s “Sk8er Boi” could be googled in one picture, this is the guy that would come up. He’s hitting every stereotypical checkmark, from the Beiber haircut to the oversized graphic sweater.

Look As Scary As Possible

hot topic store manager poses with two kids
Photo Credit: mommy-im-scared / Reddit

This is two friends posing with the manager from the Hot Topic at the mall in 2009 like he’s some sort of celebrity simply because he works at the only store that supports their haunting fashion choice.

There Is Hope

old couple's photo at a diner
Photo Credit: kiedomandy / Reddit

This photo is proof that even the most awkward of teenagers and those who thought using up a whole pencil eyeliner a day while dating a man who covers his eyes with bangs on purpose, can all turn out alright.

This couple, for example, is now married with a two-month-old daughter.

Nothing Like Good Ol’ Teenage Angst

guy with emo haircut sitting on dock dramatically looking over water
Photo Credit: Reddit / cohonka

I feel like every single person had at least one or two horribly embarrassing photoshoots with their friends where they took angsty photos of themselves. It was a rite of passage.

Her Haircut Added 20 Years To Her Life

girl with short haircut holding drink looks like she's almost 40
Photo Credit: Reddit / meerCat232

Believe it or not, the woman in this photo was 18 years old when it was taken. I don’t know if it’s the haircut or her smile in the picture, but she looks like she’s on her way to pick up the kids from school.

Ready To Head To The Function

group of teens all in goth/emo clothing with a mom behind them
Photo Credit: Reddit / shewolfkitty

The person who posted this explained that they took this photo with all of their friends before heading to a concert in 2006—and yes, her mom was in the background ready to drive them there in the minivan.

All Is Fair In Love

guy with eyes rimmed in black eyeliner, black fingerless gloves and nail polish
Photo Credit: Reddit / Dragonknight247

This guy explained that he had a crush on an emo girl in the ninth grade and so, in order to get her attention, he put on this entire look—nail polish and all.

In Church?!?

Photo Credit: Reddit / BeanBagSaucer

This girl, to show off her rebellious side at 13 years old, decided to throw up a “devil horn” gesture in a photo at her Catholic confirmation. Also, her grandma sewed her dress.

Graduation Is A Special Time

woman dressed in golf attire with no shoes posing with a club
Photo Credit: Reddit / llama_laughter

This girl, for some reason, chose this outfit, golf club-prop, and a specific pose with her senior photos in high school. She also has no idea why she isn’t wearing shoes.