13 Most Uncomfortable Things We Wore In The ’90s

I was a child during the ’90s, meaning I grew up during the best decade ever. The snacks were better, the TV shows supreme, and don’t even get me started on the movies. I was Clarissa from Clarissa Explains It All. Shawn from Boy Meets World was my boyfriend, he just didn’t know it yet. Rachel Green was hair goals, Buffy was attitude goals, and All That was squad goals. Can we bring these things back again?

Whoever said “fashion before comfort” clearly lived through the ’90s, since every major trend had something incredibly uncomfortable to do with it. Chokers, big, blown out hair, and jelly sandals all made for uncomfortable ’90s fashion. But boy, did they look good, considering this past year has been all about reliving the golden age of fashion.

But, beyond pop culture, fashion is really where it was at. Flannels, platform flip flops, mini skirts, Doc Martens, skater dresses, and of course, jelly shoes were all the rage. We were just cooler back then with the “I don’t care” attitude. Brown lipstick, metallic eyeshadow, and frosted lipstick thrived in the ’90s, and now, we’re trying everything to get it all back.

But we have to admit, though these looked hella cute, they weren’t exactly comfortable. While loose flannels and combat boots were comfortable and easy, most looks required extra time, effort, and a little pain.

1. Jelly Shoes

Listen, I was the queen of jelly shoes. I had them since I was three years old — they were a red pair with yellow sunglasses on. But breaking these babies in were not easy. They cut up my feet each and every time, making my feet bleed until they were super comfy.

2. Chokers

These were so cool back in the day, but man, were they uncomfortable. Especially in the summertime, when these practically trapped heat and sweat.

3. Platforms

Platforms are of course more comfortable than stilettos, but when you’re a child/young teen/young adult in the ’90s, wearing sneakers or some sort of flat would’ve been way more comfortable. I remember I had a blue pair I insisted on always wearing, but they’d always weigh me down when I was trying to play tag or Red Rover.

4. Mom Jeans

They looked so, so good, but rode up (and still do) my butt always. In retrospect, they were probably the wrong size. My mom jeans now don’t do the same, so this was my bad.

5. Crop Tops

Crop tops were quintessential ’90s, but I was always, always cold in one. I needed those extra inches!

6. Leotards

Floral Early 90s Bodysuit, $46, etsy.com

Going to the bathroom in these were always a struggle.

7. Skinny Eyebrows

Admit it: We all had super thin brows. But that meant constant plucking. Ouch.

8. High Ponies

Topanga’s hair was always on point. But honestly, this high of a ponytail hurt when you wore it all day.

9. Glitter

Glitter practically defines the decade. But anyone that’s put it on knows that it’s nearly impossible to get off, itchy, and ends up everywhere.

10. Mini Buns

This hairstyle was lit. With style and also with pain. So many mini rubber bands. Ouch.

11. Fake Jewelry

90’s Ying Yang and Smiley Face Fake Plugs Combo Pack, $19.24, etsy.com

My mom would only allow me to have one piercing, but I wanted double for major cool points. So I bought some clip on earrings, which, in theory, are super cool. But when you’re constantly checking to make sure they haven’t fallen off, or they’re pinching your ear….Yeah, majorly uncomfortable.

12. Butterfly Clips

The more, the better. But also, the more, the more painful.

13. Jeans With The Waist Cut Off

Mariah’s jeans were everything in this video. But dang, were these uncomfortable! I remember cutting off the waistband on my jeans and constantly having to pull them up. Not ideal.

Did I take you all the way down memory lane yet? I’m seconds away from looking for my clear landline and calling my crush, all while playing Mall Madness. While I miss the ’90s dearly, I definitely don’t miss having to wear these outfits for cool points. These days, I’m all about comfort before style.

Images: Columbia Pictures, ABC