Some shoe trends are timeless classics, and others… well, they should stay in the past where they belong.
Over the last decade, we’ve seen some seriously questionable footwear choices—shoes that were impractical, unflattering, or just straight-up ugly. From weird celebrity trends to painful fashion experiments, these shoes had their moment, but we won’t be missing them anytime soon.
Let’s take a walk down regrettable shoe memory lane and say goodbye to the worst offenders!
1. Wedge Sneakers
A sneaker and a heel? What could go wrong? Everything. Wedge sneakers tried to make sporty and chic happen, but they never quite worked. Instead of being stylish, they just looked bulky, awkward, and impossible to style. Luckily, we’ve moved on to sleeker platform sneakers that actually make sense.
2. Clear PVC Heels
Blame the Kardashians and Yeezy Season 1 for this one. These see-through plastic nightmares fogged up, trapped sweat, and made your feet look like they were on display in a museum exhibit. They also turned yellow over time and were impossible to walk in without slipping. A fashion fail from every angle.
3. Peep-Toe Booties
A bootie is great. A peep-toe heel is fine. But a peep-toe bootie? A confused, impractical mess. These shoes made no sense for any season—too hot for summer, too cold for winter, and just awkward all year long. Let’s leave this 2014 blogger staple in the past.
4. Dad Sneakers (The Extreme Ones)
Some chunky sneakers can be cool (shoutout to the Nike Air Monarch and New Balance 990), but the Balenciaga Triple S-style clown shoes? A disaster. These ultra-chunky, orthopedic-looking sneakers made every foot look three sizes bigger. Fashion girls tried to make them work, but let’s be honest—they were ugly from the start.
5. Sock Sneakers
Luxury brands pushed sock sneakers hard (looking at you, Balenciaga Speed Trainer), but they never looked as good as we thought they did. They were too tight, too flimsy, and made every outfit look like a failed attempt at athleisure. Plus, they weren’t even comfortable—so what was the point?
6. Platform Flip-Flops
A cursed relic from the early 2000s that somehow made a comeback. Platform flip-flops were clunky, uncomfortable, and a rolled ankle waiting to happen. They might have worked for a Lizzie McGuire moment in 2003, but in the 2020s? Hard pass.
7. Micro-Heeled Kitten Mules
There’s nothing wrong with a good kitten heel, but the super tiny, flimsy mules of the past decade? They felt awkwardly incomplete, like the designer forgot to finish the shoe. They also made every foot look weirdly long, which is never a good thing.
8. Transparent Lucite Platforms
These shoes looked like they belonged in a 2000s nightclub, yet somehow, they reappeared on red carpets in the late 2010s. Clear lucite platforms gave off stripper shoe energy, and not in a fun way. They were too tall, too tacky, and way too uncomfortable.
9. Thigh-High Stiletto Boots (That Were Impossible to Walk In)
There’s a reason Ariana Grande had to be carried while wearing these. Super-skinny, ultra-tight thigh-high boots looked dramatic but were painful, stiff, and required serious core strength to walk in. If a shoe makes basic movement difficult, it’s a fashion fail.
10. Overly Embellished Sneakers
Adding a few cool details to sneakers? Great. Covering them in rhinestones, glitter, chains, and unnecessary patches? A hot mess. The past decade gave us too many sneakers trying too hard—if your shoes could double as an arts-and-crafts project, it was time to rethink your choices.
11. Pointless Fur Slides
Luxury brands loved these, but did anyone else actually like wearing fur slides? They were hot in the summer, impractical in the winter, and made your feet look like they were being attacked by Muppets. If your shoes require constant brushing and fluffing, they’re not worth it.
12. Glitter Ugg Boots
Regular Uggs already divided the fashion world, but glitter-covered Uggs? No one asked for this. They shed glitter everywhere, got scratched up within two wears, and somehow made an already chunky boot look even bulkier. Thankfully, we moved on.
13. Clog Heels from the Early 2010s Revival
The clog heel comeback of the early 2010s was not the moment. These shoes were clunky, weirdly heavy, and somehow both too casual and too formal at the same time. The modern clog has improved, but the old versions? They can stay buried.
14. Pointy Loafers with Massive Metal Hardware
For a while, every brand tried to make pointy loafers with oversized metal bits happen. Instead of looking chic and timeless, they just looked stiff, heavy, and impractical. Loafers are back in style now, but the past decade’s over-designed versions? Let’s pretend they never existed.
15. Chunky Velcro Dad Sandals (The Wrong Kind)
Some dad sandals are trendy, but the extra-bulky, orthopedic-looking ones with giant Velcro straps? Instant regret. These shoes made even the most stylish outfits look like a forced “ugly chic” experiment gone wrong. If you love comfort, modern hiking-style sandals or sleek sporty slides are way better choices.