20 Awkward Trends from the Past We Thought Were Cool
Hindsight is 20/20, and looking back, some past trends make us wonder, “What were we thinking?”
- Chris Graciano
- 4 min read
Every era has its share of questionable fashion choices. What once seemed trendy and cutting-edge now feels cringeworthy or outright embarrassing. From frosted tips to extreme low-rise jeans, here are 20 trends we embraced wholeheartedly—only to regret later.
1. Frosted Tips
greyloch greylo on Flickr
In the late ‘90s and early 2000s, guys everywhere bleached just the top layer of their hair, leaving them looking like human porcupines. Boy bands popularized the style, making it a staple of teenage rebellion.
2. Low-Rise Jeans
Keymeulen on Wikimedia Commons
These pants sat dangerously low on the hips, leaving little to the imagination and plenty of room for wardrobe malfunctions. They were everywhere in the early 2000s, championed by pop stars and reality TV icons.
3. Overly Thin Eyebrows
Eva Rinaldi on Wikimedia Commons
The ‘90s and early 2000s had people plucking their eyebrows into barely-there lines. It seemed fashionable then, but many who overdid it found their brows never quite grew back.
4. Ed Hardy Everything
Mike Mozart on Flickr
Loud, rhinestone-covered T-shirts with over-the-top graphics became a status symbol in the mid-2000s. Celebrities rocked them, and soon, so did everyone else.
5. JNCO Jeans
duhews dfbas on Pexels
These ridiculously wide-legged jeans made wearers look like they were smuggling parachutes. Popular in the ‘90s rave and skater scenes, they were a nightmare to walk in and even worse in the rain.
6. Popcorn Shirts
Ali Pazani on Pexels
Tiny, crinkled tops that expanded when worn seemed futuristic at the time. They were everywhere in the early 2000s, but looking back, they resembled wrinkled fabric disasters.
7. Puka Shell Necklaces
Behnam Ramezani on Pexels
Thanks to surf culture and early 2000s teen heartthrobs, puka shell necklaces were a must-have accessory. Whether you actually surfed or not, wearing one made you feel effortlessly cool.
8. Dresses Over Jeans
Liza Bakay on Pexels
For some reason, layering a mini dress over denim jeans was the peak of early 2000s fashion. This awkward mash-up made no sense but was seen everywhere on red carpets and magazines.
9. Tribal Tattoos
Pitbull Tattoo Thailand on Flickr
These bold, black-ink designs became wildly popular in the ‘90s and early 2000s, especially among guys trying to look tough. Unfortunately, most people didn’t know the cultural significance of the patterns and just picked designs from a tattoo shop wall.
10. Shutter Shades
Dtwilkerson on Wikimedia Commons
Made famous by Kanye West, these plastic sunglasses had slatted lenses that completely blocked your vision. Despite being practically useless, they became a party must-have in the late 2000s.
11. Velour Tracksuits
William Krause on Unsplash
Juicy Couture tracksuits were the uniform of the mid-2000s, especially for celebrities. Plush, colorful, and often featuring rhinestone logos, they were both comfy and flashy.
12. Flip Phone Antennas
User:Tkgd2007 on Wikimedia Commons
Before smartphones, people customized their flip phones with glowing antennas, charms, and rhinestones. The flashier, the better. Looking back, it’s hilarious how much effort went into personalizing something so basic.
13. Extreme Spiky Hair
Michelangelo Buonarroti on Pexels
Somewhere between punk and anime, extreme gelled-up spikes ruled the early 2000s. Guys would use entire bottles of hair gel to ensure their spikes remained strong.
14. Tiny Scarves
kaylkels on Flickr
In the 2000s, scarves weren’t worn for warmth but as tiny, useless fashion statements. They were often too short or too thin to actually serve a purpose.
15. Chain Wallets
Charivario on Wikimedia Commons
Worn by skaters and punk rockers in the ‘90s and early 2000s, chain wallets were supposed to keep your money safe. In reality, they were just a clunky metal nuisance that made sitting uncomfortable.
16. Tanning Beds
user:Janneman on Wikimedia Commons
Before people knew the dangers of UV exposure, tanning beds were a must for maintaining a year-round glow. It wasn’t until later that people realized they were essentially slow-cooking their skin.
17. Guy Liner
Izzie Button on Flickr
Men wearing heavy black eyeliner became a major trend during the emo phase of the 2000s. Bands like My Chemical Romance inspired teens everywhere to smudge on dark makeup.
18. Bedazzled Everything
Rosenfeld Media on Wikimedia Commons
From cell phones to handbags, if they could be covered in rhinestones, they were. The early 2000s were all about unnecessary sparkle, and celebrities led the charge.
19. Sagging Pants
Ed Yourdon on Flickr
Wearing pants way below the waist was a major trend, especially in the ‘90s and early 2000s hip-hop scene. It was meant to be rebellious but mostly made walking difficult.
20. Feather Hair Extensions
Hank Hession on Flickr
For a brief moment in the early 2010s, people were clipping real bird feathers into their hair. Inspired by boho-chic fashion, they quickly became a salon staple.