20 Photos From the Past That Made Their Owners Laugh and Cringe at the Same Time

2 years ago

Time runs fast and trends change rapidly. And what we thought was cool back then may seem silly or cringe-worthy today. Proof of this can be seen in how we feel when we come across our old photos. Most of them make us feel embarrassed of our past styles, but they also remind us of a fun and carefree period in our lives.

Get ready to laugh and wince as Now I’ve Seen Everything presents 20 relatable photos of people that will remind you of your younger years as well.

1. “Desperately trying to be ’metal’ in 1988/89. I cut and dyed my own mullet. Also took a razor to my brows for some reason.”

2. “Here are my poor parents being nice to me back in 1987 during my Billy Idol skateboarding phase.”

3. “Me, a straight female, trying to impress my crush by being one of the guys, I’m on the right.”

4. “My mom calls this photo a family heirloom. It was taken 16 years ago: it’s me (female, 13) and my boyfriend (male, 13) at the Olive Garden.”

5. “In case you’re wondering, yes, I was home-schooled.”

6. “10-year-old me, reaching peak coolness: a purple jogging suit with a ninja shirt and high-top Adidas sneakers (1990)”

7. “I was so proud of how cool I looked with this background in 1994.”

8. “Me in 1988 with a VW Bug I bought for $50”

“I made a BEACH PATROL stencil out of newspapers, then painted it with a can of spray paint in my driveway.”

9. “Out at the rock club with the crew sometime around 2001. I can’t believe we used to take a 30-minute bus ride to the city whilst dressed up like this.”

10. “2011, I was 14 — I thought I was the coolest and most emo person ever.”

11. “The baby face, the deer in the headlights stare, the loudest T-shirt I could find — not shown is my matching jean shorts.”

12. “Had to let Myspace know I could play drums somehow.”

13. “Ladies and gentlemen, I present to you my eighth-grade picture from 1989. Behold the hair, the earrings, and the acid wash.”

14. “In high school (2006-ish), I thought a Batman belt buckle and a sideways red robotics hat was cool.”

15. “A studded belt, a beaded necklace, a rave bracelet, skinny jeans, and teased hair: meet 16-year-old me, circa 2010.”

16. “Wore a beanie for 2 days to get my greasy hair to cover my eyes. Also had no idea how to play that bass.”

17. “Me at 12 or 13, thinking I was cool posing with a random car”

18. “Still waiting for my glow-up...”

19. “I was the absolute coolest dude in the late ’90s.”

20. “I wore this Matrix-inspired outfit to school in 2008.”

Do you also have embarrassing photos that you used to think were cool? Would you be able to share them with the Internet like the people from the post, or is it a part of your life that you want to remain hidden?


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