You know that feeling when someone’s outfit is technically trendy but just… trying way too hard? Yeah, shoes can do that too. No matter how expensive or hyped they are, some styles just scream effort in all the wrong ways, making your whole outfit look messy, overdone, or straight-up outdated.
The secret to looking effortlessly chic? Shoes that elevate, not dominate, your look. And trust me, the ones on this list do the exact opposite. From overcomplicated designs to trends that should’ve stayed in the past, these 13 try-hard shoes will instantly make you look less put-together—no matter how hard you try. Let’s get into it.
1. Overly Worn-Out Ballet Flats
Ballet flats can be chic—but only if they look fresh. When they’re floppy, stretched out, or have scuffed-up toes, they instantly make an outfit look lazy and tired. A polished alternative? Structured, pointed-toe flats or slingbacks that still give you comfort but with a put-together edge.
2. Cheap, Paper-Thin Flip-Flops
Unless you’re poolside or at the beach, flimsy rubber flip-flops do nothing for your outfit. They make even the chicest summer looks feel unrefined and last-minute. Instead, opt for sleek slides, leather sandals, or espadrilles—you’ll still get that effortless vibe but with a more polished finish.
3. Slouchy, Overworn Ugg Boots
We get it—Uggs are cozy, but when they’re flattened, dirty, or sagging at the ankles, they make you look messy and unkempt. A better option? A sleek ankle boot or structured shearling-lined boot that still gives you warmth but keeps things elevated.
4. Super Clunky Dad Sneakers (The Over-the-Top Kind)
Chunky sneakers had their moment, but when they go too far into orthopedic territory, they start looking awkward instead of fashion-forward. A more stylish take? Sleek, minimal sneakers like Adidas Sambas, New Balance 550s, or clean white leather kicks.
5. Worn-Out or Dirty White Sneakers
White sneakers can be a wardrobe staple, but if they’re scuffed, yellowing, or covered in stains, they instantly cheapen your look. If you want to keep that effortlessly cool aesthetic, make sure they’re clean and in good condition—or swap them out for a fresh new pair.
6. Peep-Toe Booties
These had their moment in the early 2010s, but now they just look confused and outdated. The mix of a boot with an open toe doesn’t make much sense seasonally or style-wise. Instead, go for classic ankle boots, sleek-heeled sandals, or structured pumps that keep things clean and polished.
7. Super Tall Platform Flip-Flops
Unless you’re filming a Y2K nostalgia video, it’s time to retire these. They instantly make any look feel gimmicky and juvenile—not exactly the vibe if you’re aiming for polished. Instead, opt for elegant, minimal sandals that elongate your legs without looking cartoonish.
8. Overly Embellished Sneakers
Think sneakers drowning in rhinestones, metallics, glitter, and bedazzled logos. While they may have had a moment in the early 2010s, these days they look more like a craft project than a fashion statement. Instead, choose sneakers with modern details, like suede accents or subtle textures, for a more elevated look.
9. Extreme Pointy-Toe Stilettos
A slightly pointed toe? Chic. A toe so long and sharp it could double as a weapon? Instantly dated. These heels give off early 2000s office party energy, and not in a good way. Instead, opt for almond-toe or softly squared-off heels that feel more modern and wearable.
10. Super Slouchy, Unstructured Knee-High Boots
A well-structured knee-high boot? Timeless. A boot that flops over, slouches at the ankles, and looks deflated? Messy. Instead of going for overly relaxed and shapeless styles, stick to sleek, structured boots that hold their shape for a polished look.
11. Clogs That Look More Orthopedic Than Chic
Some modern clogs can be stylish, but when they veer into clunky, overly chunky, or nurse shoe territory, they start working against your outfit instead of enhancing it. If you love clog-inspired shoes, go for sleeker, more structured versions with a slight heel or luxe textures to keep things refined.
12. Overly Trendy, Gimmicky Shoes
You know the ones—shoes that had a viral moment but didn’t actually age well (looking at you, sock sneakers and futuristic space boots). These tend to date your outfit instead of making it feel timeless. If you want to look polished, stick to modern classics that will still be stylish five years from now.
13. Lace-Up Gladiator Sandals That Go Up to Your Knees
We all had a moment in the mid-2010s when knee-high gladiator sandals were everywhere, but let’s be honest—these shoes are a styling nightmare. The straps never stay in place, they cut into your legs, and by the end of the day, your calves look like they’ve been through a battle.
Plus, they instantly make any outfit feel overcomplicated and outdated. If you love strappy sandals, stick to sleek, minimal lace-ups that stop at the ankle.
14. Hyper-Chunky, Futuristic Sneakers
There’s statement footwear, and then there’s shoes that look like they belong in a sci-fi movie. Those ultra-chunky, over-designed sneakers with excessive layers, bizarre shapes, and unnecessary bulk? Yeah, they might turn heads, but not in a good way.
Instead of looking stylish, they make your outfit feel like it’s trying too hard to be “fashion-forward.” If you want a cool sneaker moment, go for sleek, well-structured silhouettes like classic Air Force 1s, Adidas Sambas, or New Balance 550s.