Nostalgia can be bittersweet, especially when it comes to the questionable fashion choices and habits of our younger years. These 10 fads, pulled straight from real-life regrets, show just how far we’ve come from the trends we once thought were the epitome of cool.
- Tall Tees and Livestrong Bracelets
The mid-2000s were marked by oversized “tall tees” that reached ridiculous lengths. Paired with colorful Livestrong wristbands to match these shirts, this trend screams youthful peer pressure gone wrong. The look hasn’t aged well, much like the stretchy rubber bracelets themselves.
- Chain Wallets and Safety Pins
For a generation looking to feel “edgy,” chain wallets and excessive safety pins became a staple. While some say the safety pins made them feel secure (literally and figuratively), others now wonder why they needed so much “protection.”
- JNCO Jeans and Super Baggy Pants
The baggier, the better—at least in the late ’90s and early 2000s. These jeans dragged on the ground, soaking up dirt, rain, and road salt, and were often frayed to tatters. Bonus regret: getting caught in bike chains or tripping over your own pant legs.
- Shiny Flame Button-Ups
Silky polyester shirts adorned with flames or dragons were once a symbol of middle school “coolness.” While some claim these shirts had roots in Hawaiian or Aloha fashion, their popularity among non-islanders remains a mystery (perhaps a Guy Fieri effect?).
- Double Polos with Popped Collars
Because one polo wasn’t enough, people layered two, each with its collar popped. Throw in an upside-down, backward visor, and you’ve unlocked peak cringe.
- Trucker Hats
Thanks to Ashton Kutcher and brands like Von Dutch, trucker hats became ubiquitous in the 2000s. Many regret shelling out significant amounts of money for hats that now look laughable and represent a bygone era of questionable style.
- Jeans With Holes or Tattered Bottoms
Destroyed denim was all the rage. The longer and more frayed the bottoms were, the cooler you looked. This trend often led to soaked ankles and salt-crusted jeans in the winter—proof that suffering for fashion isn’t new.
- Millennial “Thug” Phase
Suburban kids trying to emulate hip-hop culture adopted sagging pants, bling, and a “tough guy” persona that they now look back on with a mix of humor and horror. The inability to run because of sagging pants was a particular sticking point for regret.
- Button Pins and Graffiti Bags
Decorating corduroy or jean messenger bags with band buttons, patches, and Sharpie doodles seemed like a great way to express individuality. Years later, these bags serve as relics of angsty, artistic youth rather than functional accessories.
- Frosted Tips and Bleached Hair
Inspired by boy bands like NSYNC and celebrities of the early 2000s, frosted tips (spiky hair with bleached ends) were everywhere. This trend was often paired with gelled, gravity-defying hair, leaving many to cringe at old photos that scream, “I spent way too much time in the bathroom.”
These fads show that trends often don’t age gracefully. But maybe that’s the charm—remembering the wild things we once did to fit in, express ourselves, or stand out. After all, isn’t cringing at old photos just part of growing up?
