These '90s Shoes Were Uncomfortably Cool

by Marc Cuenco

I discovered my love for trendy footwear around freshman year of high school, which (thank the fashion stars) happened during the '90s. For those of us who survived to tell some of these painful podiatric tales, most '90s shoes were uncomfortable to wear. However, those blisters, cuts, and soreness seemed to be worth it every time we put on our favorite pair of shoes.

One of the most iconic shoes from the decade that gave the world Clueless, Friends, and the Spice Girls are the jelly shoes. Millions of feet donned a pair of these PVC sandals for no apparent reason other than they simply looked cool (and also very emblematic of '90s style). But the truth of the matter is, jelly shoes aren't comfy at all, otherwise, people wouldn't still be writing about their love-hate relationship with them.

There was also something about adding height in the '90s, so various types of boots were very much in style. The problem is that whether the look you were going for was punk (Dr. Martens), hip-hop (Timberlands), or club kid (Fluevogs), you surely endured discomfort with your favorite shoes from the '90s. But as soon as those blisters and sores on your feet went away, you still couldn't wait to wear them again.

Check out seven of the most uncomfortable '90s shoes that we still love to this day:

1. Jelly Shoes

These plastic beauties have a reputation as one of the most uncomfortable shoes to wear, but everyone still loves them.

2. Dr. Martens

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The iconic brand remains timeless, but unless they've been properly broken in, Dr. Martens boots can hurt.

3. Skechers 4-Wheelers

They weren't only uncomfortable for the novice wearer, but also quite dangerous.

4. Clogs

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Often made of wood with a thick sole, clogs are supposed to help your posture and make walking easier. Yeah, right.

5. Fluevogs

These funky shoes ruled the '90s club scene, but like its distant cousin the clog, they weren't very comfortable after a full night of dancing.

6. Timberlands

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These tough and durable work boots are meant to protect your feet, but they also didn't feel like walking on clouds either.

7. Platform Boots

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The Spice Girls' favorite shoes to wear took us to new heights... of discomfort. But they still looked really dope.