15 Cringe-Worthy Trends From 20 Years Ago That’ll Make You Want To Crawl Under A Rock
This post may contain affiliate links which means I will get a commission if you make a purchase at no additional cost to you. As an Amazon Associate I earn from qualifying purchases. Please read my disclosure for details.
The turn of the millennium brought several changes. We looked forward to Y2K and what it meant in the programming world. Along with this came interesting trends that are cringe-worthy today. Most of these trends were considered rites of passage for millennials and only the โcoolโ kids could do it.

WOULD YOU LIKE TO SAVE THIS?
Today, we wish we didn’t believe these trends were cool. Weโve put together 15 cringe-worthy things we all did 20 years ago. Which of these trends makes you want to crawl under a rock?
Peed In Pool
Growing up, most of us shared unspoken childhood traditionsโlike peeing in a pool. A moment of silent rebellion, masked by an innocent face and rippling water, it is a secret many carry with a mix of nostalgia and mischief. Cringe-worthy to note is that we probably swam in someoneโs pee.
Pretended to be Someone you are not
20 years ago, idolizing someone went overboard. We dressed like our favorite movie characters and imitated accents that were downright cringe.
Embarrassing Dance Moves
The early 2000s were marked with wildly embarrassing dance movesโspinning, flailing, or awkwardly grooving with zero rhythm. Distorting our facial features to dance was considered cool.
Matching Friendship Outfits
We all had squads back then we loved to wear matching accessories or shoes because we felt they were cool. Matching friendship outfits felt like the ultimate bondโdeclaring to the world, โWeโre a team!โ
Confessed to a Crush
We all look back and wonder why we had that crush! The worst part is we confessed! Confessing to a crush growing up was a mix of bravery and nervesโheart racing, rehearsed words spilling out awkwardly, and hoping for magic, even if it ended in an awkward smile or a โletโs just be friends.โ
Shared Excessively on Social Media
The social media frenzy was at its peak. We shared the dumbest thingโposting every thought, selfie, or meal, thinking the world cared as much as we did. It was a digital rite of passage, cringy but oh-so-relatable!
Related: 15 Ways Naturally Classy People Win Without Trying
Awkward Fashion Choices
Growing up meant rocking some truly questionable fashion choices we felt were cool. Over-the-top accessories, clashing colors, or trends that made no sense.
Discover stunning winter outfit ideas on my LTK Shop here.
Bad Haircuts
From DIY bangs to bowl cuts to the infamous emo swoop, we all had one bad haircut that we considered to be cool. You get additional cringe points if your hair has chunky highlights or frosted tips.
Related: Stop Making These 16 Style Mistakes That Scream Cheap
Flip Phones with Antenna
We all had that flip phone with an antenna, clicking it open or close with a dramatic snap, feeling like we were in a spy movie every time we made a call. Bonus cringe points for the dangling charms.
Related: 15 Workwear Brands To Elevate Your Style
Layered Tank Tops
Remember the layered tank top phase? Weโd pile on different colors and patterns, creating a โcoolโ and carefree look. Why wear one tank top when you can wear all the tops in your wardrobe?
Not sure what to wear this season? Discover affordable outfit ideas on my Amazon Storefront!
Big Plastic Hair Clips
Remember those big plastic hair clips? They were the ultimate accessoryโwhether holding back messy hair or just for style. The more clips you put, the fancier we felt it was.
Related: 16 Irresistible Habits Of Women Who Radiate Timeless Style
Took Selfies with Big Cameras and a Mirror
Weโve all been thereโtaking selfies in front of big mirrors, striking poses, and trying to capture our best angle. Bonus cringe points if your phone had a colorful pouch.
Related: 15 Shoe Fails That Are Sabotaging Your Style Game
Spent Money on Ringback Tones
We all believed that fancy ringback tones were entertaining. We picked ringtones that fit our personalities and let our callers vibe to the tune. Looking back, why did we waste money on this meaningless expense?
Related: 15 Shocking Funeral Outfit Disasters You Should Avoid at All Costs
Wore Mood Rings
We all rocked mood rings at some point, fascinated by how they changed color to โrevealโ our emotions. The cheap plastic could not tell our moods but we believed it could and spent money on it!
Related: 17 Luxe Amazon Finds Under $25 That Feel Expensive AF
Put Glitter on Everything
We sprinkled glitter on everythingโschool projects, notebooks, even random objectsโbecause everything just seemed better with a little sparkle. 20 years ago, glitter was magical!
Related: 15 Easy Ways to Look Instantly Put-Together
Disclaimer: This list is solely the authorโs opinion based on research and publicly available information.
Men, 15 Style Crimes That Are Killing Your Look
Stylish men are confident and attractive. They have timeless style and have figured out what look works for them. Stylish men carry themselves effortlessly, every outfit they wear looks like it was made for them.
Read it here: Men, 15 Style Crimes That Are Killing Your Look
45+ Fashionable African Dresses to Rock This Year!
What if you could own the spotlight at every event this year? These 45+ chic African dresses are designed to unleash your inner fashionista and have everyone asking, โWhere did you get that?
Watch it here: 45+ Fashionable African Dresses to Rock This Year!
100+ Modern Winter Outfits That Are Anything But Frumpy
Still reaching for the same tired winter looks? Donโt let frumpy outfits define your styleโthese 100+ modern winter outfits will keep you warm and effortlessly stylish. You deserve better than boring this season!
Find it here: 100+ Modern Winter Outfits That Are Anything But Frumpy