Our closets tell a story — snapshots of our past selves and the versions of us we’re still becoming. Instead of asking ‘What was I thinking?’ try asking, ‘What did this version of me need?’
Fashion moves fast, doesn’t it?
One minute we’re proudly strutting around in something that feels fresh and modern, and the next we’re wondering how we ever thought that outfit worked.
It’s not about judging past choices either.
In fact, I see it as a kind of playful time capsule that shows us who we were and who we’re becoming.
And if you’ve ever looked in your closet and felt that twinge of “Wait… didn’t this used to be cool?” you’re in good company.
I’ve had those moments too.
After all, I still have a jacket my sister lovingly refers to as “the relic.”
So let’s talk about some of those once-trendy pieces that now feel a little stuck in the past.
And perhaps even more importantly, why understanding these shifts can help us dress in a way that reflects who we are now rather than who we used to be.
Let’s jump in.
1) Cold-shoulder tops
Do you remember these?
The tops with little cutouts that exposed each shoulder?
For a while, they were everywhere. I had one in blush pink that I wore to at least five different brunches.
But here’s the thing: once a trend becomes too ubiquitous, it tends to fade quickly.
These tops now carry a kind of unmistakable timestamp.
They’re not terrible, just unmistakably “2018 energy.”
If you still love the neckline or the shape, consider opting for off-the-shoulder or asymmetrical cuts instead.
They feel sleeker, more intentional, and not tied to a specific moment in pop culture.
2) Tiny sunglasses
Some trends fade subtly.
Tiny sunglasses, though?
They fell off a cliff.
Five years ago, these micro-shades were all over Instagram.
Celebrities wore them like props in a high-fashion performance.
And yes, I bought a pair.
I wanted to feel edgy and modern, even if I couldn’t see much through them.
Looking back, I can’t help but laugh.
They weren’t practical, and they didn’t flatter most face shapes.
Today, we’re gravitating toward eyewear that feels more wearable, protective, and timeless.
So if you still have a pair tucked in a drawer, it might be time to thank them for their service and move on.
3) Chunky dad sneakers
This one might sting.
The exaggerated “dad sneaker” look had its moment, riding that wave of ironic fashion that mixed nostalgia with streetwear.
And while comfort will always be a priority (especially for me since I trail run and love supportive shoes), the aesthetic now feels a bit costume-y.
I sometimes ask myself before getting dressed: “Does this piece highlight my authenticity or distract from it?”
Those super bulky sneakers tend to fall into the second category.
Sleeker sneakers with clean lines have taken their place.
They’re just as comfortable but a lot more current.
4) Super distressed denim
A little distressing can add character to a pair of jeans.
But five years ago, extremes were in style. I’m talking rips so wide you basically had built-in air conditioning.
Back then, it seemed rebellious and carefree. Now? It leans theatrical.
One of my coaching clients once told me she kept wearing her heavily distressed jeans even though she didn’t love them anymore because they were expensive when she bought them.
I suggested a quick mindset shift: instead of asking, “Did I get my money’s worth?” try asking, “Does this piece represent where I am today?”
Her answer was clear.
She donated them the next day.
If you still enjoy texture or uniqueness in your denim, moderate distressing or interesting seams can give you that without looking outdated.
5) Belt bags worn crossbody
Let me clarify: belt bags themselves are not outdated.
They’re practical and can look great.
What feels dated is that specific crossbody slung-across-the-chest styling that was a street-style staple a few years ago.
It became so trendy that it bordered on uniform.
And once something becomes uniform, it stops feeling fresh.
A simple tweak can make the difference: wear belt bags at the waist again or try a minimal sling bag with a subtle profile.
Those feel much more aligned with the quieter, pared-back look that’s gaining traction now.
6) Oversized logo tees
I still remember seeing oversized tees with huge logos plastered across the front everywhere.
Maybe you had one too.
They were fun, easy, and great for those morning “I need coffee before I can function” days.
But fashion has shifted toward pieces that whisper rather than shout.
And giant branding tends to scream.
A question I often ask readers is: “Does this help me express my identity or someone else’s?”
Oversized logo tees usually fall into the latter category.
If you enjoy relaxed silhouettes, that’s still totally in.
Just choose cleaner designs or subtle graphics that look intentional rather than trendy.
7) Neon everything
Neon had such a strong moment that it was honestly hard to avoid.
Activewear, bags, shoes, even blazers were glowing like highlighters.
I remember teaching a workshop once, and half the room showed up in neon green workout tops.
Here’s the challenge with neon: it causes visual fatigue.
Since it’s so loud, it has a short trend shelf life.
Today, the palette has shifted to softer tones and earthy neutrals that feel gentler and more versatile.
If you still crave brightness, try rich jewel tones.
They’re bold but not blinding.
8) Plastic clear accessories
Clear heels, clear bags, clear belts.
At the time, they felt futuristic.
But trends built on novelty alone rarely age well.
I’ll be honest: I never warmed up to clear shoes.
They fogged, they squeaked, and they always reminded me of those childhood dress-up stilettos.
But I had friends who adored them and now can’t look at them without feeling the urge to hide them in the darkest corner of their closets.
Transparent accessories now read less as “modern” and more as “throwback to a very specific year.”
If you like the minimalist vibe, try glass-bead jewelry or structured neutral bags.
They give the same sense of clean simplicity, with none of the timestamp.
9) Peplum tops
Peplum silhouettes swing in and out of fashion every few years.
But the specific peplum that trended five years ago, with its stiff, flouncy flare at the waist, now looks distinctly outdated.
These tops were everywhere, and they did a great job of creating an hourglass shape.
The problem is that once a silhouette becomes synonymous with a particular era, it stops feeling current.
What’s trending now leans more toward relaxed tailoring and fluid lines.
Pieces that drape rather than jut.
Clothing that works with your natural shape instead of sculpting it with rigid seams.
And if you still like a little waist definition, wrap tops or lightly structured blouses offer shape without the cartoonish bump of an exaggerated peplum.
Final thoughts
It’s tempting to look at outdated clothes and cringe a little, but I think there’s a better perspective.
Our closets tell a story.
They’re snapshots of our past selves, our experiments, our moods, and our moments of boldness and insecurity.
Instead of asking “What was I thinking?” maybe try asking, “What did this version of me need?”
Fashion shifts because we shift.
And letting go of pieces that no longer feel aligned isn’t about chasing trends. It’s about making room for the person you are today.
So if you recognized a few items on this list, take it as an invitation.
Not to judge. Not to rush to buy something new.
But simply to get curious about how you want to show up in your clothes now.
And who knows?
A few years from today, you might look back and smile at the choices you’re making right now too.
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