Fashion is always evolving, and while some trends make a stylish comeback, others just scream outdated. The wrong shoes can instantly drag your outfit back a decade (or two)—and not in a cool, retro way.
From overdone 2010s styles to questionable Y2K footwear choices, these 15 shoes will date your look in seconds. If you’re still holding onto these, it might be time for a style refresh.
Let’s go through the biggest offenders—because your outfit deserves better!
1. Wedge Sneakers
Ah, the early 2010s Tumblr era, where we all thought hidden wedges in sneakers made sense. Spoiler alert: they didn’t. Once a favorite of celebs like Beyoncé (who, to be fair, can pull off anything), these shoes now just feel clunky and awkward.
If you want a sporty-chic look, trade them for sleek platform sneakers that actually make sense.
2. Peep-Toe Booties
Once upon a time, these were on every fashion blogger’s feet, but now? They just feel off. The mix of an open-toe with a wintery boot silhouette no longer makes sense, and the short, chunky heel feels way too 2014.
If you love booties, swap them for modern ankle boots with a sleek pointed-toe or sculptural heel.
3. Ballet Flats with No Support
Yes, ballet flats can be timeless, but those super-thin, rounded-toe versions from the 2000s? They look outdated and are terrible for your feet. If your go-to flats are giving suburban mall energy, it’s time for an upgrade. Opt for structured flats with an elegant pointed toe, chic slingbacks, or even luxe loafers for a fresher look.
4. Gladiator Sandals
The boho queen aesthetic of 2010 called—it wants its sandals back. Gladiator sandals, especially the knee-high versions, instantly make any outfit feel like it’s stuck in a Coachella time capsule. Instead, go for minimalist strappy sandals or modern lace-up styles that feel effortless without looking overdone.
5. Platform Flip-Flops
Unless you’re starring in a 2003 teen rom-com, it’s time to let these go. Platform flip-flops had their moment in peak Y2K, but now they just feel dated and clunky. If you want height in a casual sandal, go for modern flatform slides or chunky-soled sandals instead.
6. Overly Bedazzled Sneakers
We all love a little sparkle, but when your sneakers look like they were attacked by a glue gun full of rhinestones, it’s time to move on. Super bedazzled, metallic, or glitter-covered sneakers scream 2012 department store fashion—and not in a cool, ironic way.
If you love a bold sneaker, try metallic accents, sleek monochrome designs, or fun colorways that don’t look like a craft project.
7. Cork Wedge Sandals
There was a time when cork wedge sandals were the ultimate summer staple, but let’s be real—they instantly age an outfit now. The combination of bulky cork soles and thick straps screams mid-2010s brunch outfit.
If you love wedges, switch to espadrille wedges or sleek block-heeled sandals for a modern touch.
8. Extreme Pointy-Toe Heels
A slight pointy toe? Always chic. A dagger-sharp toe that looks like it could poke someone’s eye out? Not so much. The hyper-exaggerated pointy-toe heels of the early 2000s feel outdated and harsh. A more modern almond or softly pointed toe will give you the same elegant effect without looking too retro.
9. Square-Toe Heels from the ’90s (the Bad Kind)
Not to be confused with trendy modern square-toe styles, the heavy, blocky square-toe heels from the late ’90s and early 2000s just look outdated. They have an awkward shape that instantly drags your outfit back to office fashion from 1998.
If you love square toes, go for sleeker, refined silhouettes that feel intentional and stylish.
10. Kitten Heel Mules with No Personality
A good kitten heel? Chic. A flimsy, basic kitten heel mule from the early 2000s? Not so much. If your low-heeled mules look like something you’d find at the back of a clearance rack from 15 years ago, it’s time for an upgrade. Choose sculptural heels, bold colors, or unique details to keep things current.
11. Converse with Worn-Out Laces and Yellowing Rubber
A fresh pair of Converse? Cool and timeless. A pair that looks like it survived 2008 Warped Tour and never left your closet since? Not so much. If your classic sneakers are looking extra beat-up, either give them a good clean or invest in a fresh pair—because scuffed and discolored doesn’t read “vintage,” it just reads old.
12. Clog Heels from the 2010s Revival
The clog-heel trend tried to make a comeback in the early 2010s, but let’s be real—it never quite worked. These shoes instantly date an outfit, making even the trendiest looks feel off. If you love a chunky, comfortable shoe, try modern platform loafers or sleek wooden mules for a fresh, elevated style.
13. Chunky Velcro Sandals (The Not-Cool Kind)
Sporty Velcro sandals can work if styled right, but the bulky, orthopedic-looking ones from the 2000s? Instantly dated. These shoes give off tourist-at-Disney vibes, and not in the cool, ironic way. If you want comfy sandals, look for sleek hiking-style sandals or trendy dad sandals instead.
14. Outdated Ankle Booties with a Super Short Shaft
Ankle boots are a forever staple, but those low-cut, awkwardly shaped booties from the early 2010s can instantly make an outfit feel outdated. They don’t hit at a flattering height and tend to cut off the ankle in an unflattering way. Instead, opt for taller, sleeker ankle boots that elongate the leg.
15. Mary Janes with Chunky Low Heels
Mary Janes are having a moment again, but not all versions are trendy. The clunky, low-heeled versions from the early 2000s just feel dated. If you love the Mary Jane aesthetic, go for a modern take—like platform versions, patent finishes, or bold buckle details.