We’ve all done it—put on a pair of gorgeous but painful shoes, thinking we could handle a few hours of suffering for the sake of fashion.
But some shoes take it to the next level of foot torture. From impossible-to-walk-in heels to back-breaking flats, these 15 uncomfortable shoes remind us that beauty is pain—but sometimes, it’s just not worth it.
Would you still wear any of these? Let’s rank them from mildly annoying to pure agony!
15. Converse Chuck Taylors (Before the Comfort Update)
Classic? Yes. Comfortable? Absolutely not. The OG Converse Chucks had zero arch support, no cushioning, and stiff canvas that made your feet feel like they were wrapped in cardboard. Unless you added insoles (or had feet of steel), these were basically fashionable foot traps.
14. Ballet Flats with No Support
Flats should be comfortable, right? Wrong. Those flimsy, paper-thin ballet flats from the early 2000s gave no support, no padding, and no protection from the ground beneath you. Walking on concrete? Felt like stepping on LEGOs. After a day in these, your feet were basically screaming for a foot massage.
13. Flip-Flops (For All-Day Wear)
Flip-flops are fine for the beach, but wearing them all day long? That’s a recipe for blisters, sore arches, and constant foot slippage. The lack of support made every step feel like a struggle, and if you walked too fast? That slap-slap noise was both embarrassing and a sign of future foot pain.
12. Wooden Clogs
The OG version of a foot torture device, wooden clogs were stiff, unforgiving, and completely lacking in flexibility. Every step felt like you were clunking around in medieval footwear—because, well, they were originally made centuries ago. Cute? Sometimes. Comfortable? Never.
11. Uggs (Without Socks, in Warm Weather)
Uggs are cozy in theory, but wearing them without socks (or in hot weather) turned them into a sweaty, foot-slipping nightmare. They also offered zero arch support, so after a few hours, your feet were begging for real shoes. And let’s not forget the dreaded stretched-out heel—once that happened, they became impossible to walk in properly.
10. Pointy-Toe Stilettos
Pointy-toe stilettos are the ultimate power move, but after a few hours? Your toes are crushed into oblivion. Walking in them felt like tiptoeing across hot coals, and let’s not even discuss what they did to your pinky toe. If you managed to survive a full night in these without taking them off, you deserved a medal for endurance.
9. Jelly Sandals
The ultimate ’90s throwback, but let’s be real—these plastic foot prisons gave us sweaty, blistered feet within minutes. The straps dug into your skin, and once they got wet? Forget it. Every step turned into a slippery, squeaky nightmare. Adorable? Yes. Wearable? Only if you enjoyed foot pain.
8. Thigh-High Stiletto Boots
Ariana Grande may have looked iconic in them, but thigh-high stiletto boots were impossible to walk in. Between the tight fit, lack of flexibility, and constant battle to keep them from sliding down, they were pure suffering from the knees down. The only way to survive the night? Getting carried like Ari herself.
7. Sky-High Platform Flip-Flops
A questionable Y2K trend that made walking feel like an extreme sport, platform flip-flops were wobbly, unstable, and just waiting to betray you. One wrong step, and you were twisting an ankle or toppling over completely. If you survived wearing these without a rolled ankle, consider yourself lucky.
6. Corset Heels
Heels are already hard enough to walk in, but then designers decided to lace them up like a Victorian corset? Not only did they suffocate your feet, but if you tied them too tight, your circulation was basically cut off by hour two. And good luck trying to take them off in a hurry—undoing all those laces took forever.
5. Clear PVC Heels
Nothing says “regret” like realizing your feet are slowly suffocating in foggy plastic shoes. These see-through heels were sweaty, slippery, and prone to turning yellow over time. Walking in them felt like wearing a personal foot sauna, and let’s not forget the blisters from that stiff plastic digging into your skin.
4. Lace-Up Gladiator Sandals
A Coachella-era disaster, gladiator sandals were pure pain from the second you put them on. The long laces never stayed in place, constantly dug into your legs, and required 20 minutes to properly lace up. And the worst part? They always slid down mid-walk, turning your legs into a tangled mess.
3. 10-Inch Ballet Heels
Yes, these exist—and yes, they are literal foot torture. Inspired by actual ballet pointe shoes, these heels force your feet into a painful, unnatural arch that makes walking nearly impossible. They’re more of a fashion statement than an actual shoe, but either way? They deserve their spot near the top of this list.
2. Alexander McQueen Armadillo Boots
These gravity-defying, alien-looking shoes were stunning but impossible to walk in. With a towering 12-inch curved platform, they made walking feel like an Olympic-level balancing act. Lady Gaga made them iconic, but let’s be real—they were more of an art piece than actual footwear.
1. 18-Inch Heel Guinness World Record Shoes
Topping the list are the tallest high heels ever made—18-inch monstrosities so extreme, you needed a team to help you stand up in them. No human should be expected to walk in shoes taller than a small child. If a shoe comes with an actual injury warning, it belongs at #1 on the list of foot torture devices.