There’s an unspoken pressure that haunts many of us when we get dressed: I need to get it right. Right color, right fit, right trend, right vibe. The result? We play it safe. We buy what’s trending, copy what others wear, and slowly chip away at the joy and creativity of dressing.
But here’s the truth: style doesn’t come from getting it right the first time. It comes from getting it wrong a hundred times, then suddenly… getting it right for you.
Every stylish person you admire has been through a phase they now cringe at. The wide belts. The random hats. The aggressively distressed jeans. They’ve all been there—and thank goodness. Because without that trial-and-error process, they’d never have carved out a look that feels real, effortless, and unmistakably theirs.
So let’s set the record straight: fashion “mistakes” are actually stepping stones. And trying—really trying—is the only way to get anywhere interesting.
Why Playing It Safe Holds You Back
Minimal wardrobes, curated Pinterest boards, and capsule closets are all the rage. And while there’s nothing wrong with clean lines and neutrals, there’s something dangerous about chasing perfection instead of personality.
Trying too hard to “get it right” leads to paralysis. You avoid bold colors because you’re “not sure they suit you.” You don’t try wide-leg pants because you “don’t know how to style them.” You stick with black-on-black-on-black because it feels safe.
But playing it safe means you’re dressing for approval, not expression. And no one ever developed a personal style by following rules they didn’t write.
The Power of the Style Misstep
Let’s reframe the so-called “failures.” The clashing outfit that made you feel self-conscious? That was you testing boundaries. The trendy piece that looked amazing online but wrong on you? That was you learning your proportions. The expensive jacket that just didn’t feel you? That was you discovering your true taste.
Style missteps are data points. They’re clues. They’re the only way to figure out what works—and more importantly, what feels right.
Try, Fail, Refine: A Stylish Evolution
Phase 1: Experimentation Without Judgment
This is where the fun begins. Say yes to strange color combos. Try silhouettes you’ve never touched. Mix vintage with designer, masculine with romantic, sporty with preppy. Don’t aim for polished—aim for curious.
Go try that neon green top from Ganni you’re not sure about. Slip into those sculptural heels from Nodaleto that look intimidating but oddly intriguing. Layer a sheer blouse from Cecilie Bahnsen over a casual ribbed tank just to see what happens.
You’re not building your forever closet in this phase—you’re exploring your options.
Phase 2: Pay Attention to the Feeling
Forget how it looks in the mirror for a second. How does it feel?
Do you keep adjusting that plunging neckline? Maybe you’re more of a mock-neck person.
Do you feel powerful in structured pieces like The Frankie Shop’s boxy blazers?
Do soft, drapey silhouettes like those from Lemaire or Low Classic make you feel calm and in control?
Your body has a style memory. It knows what feels natural and what feels like costume. Trust it.
Phase 3: Declutter Without Guilt
Once you’ve tried a range of things—some brilliant, some questionable—it’s time to edit. Not everything deserves a long-term spot in your wardrobe. But everything taught you something.
Let go of pieces that:
Never leave the hanger
You feel “meh” in, even if they’re trendy
Require too much styling effort for real life
Keep pieces that:
Feel effortless
Make you want to walk with purpose
You reach for on autopilot
This is where brands like Totême, Raey, Nanushka, and COS start to shine. Their elevated basics and intelligent design work as the foundation of a style that’s truly yours.
Real Style Is Built on Personality, Not Perfection
When someone walks into a room and you instantly clock their style—it’s never because they followed a template. It’s because they’ve committed to an aesthetic identity. And aesthetic identity takes time. It takes effort. It takes wrong turns and weird phases and outfits that looked way better in your head.
But once you’ve arrived, it’s magic. You’ll know exactly how to mix your Arket structured trousers with your worn-in vintage tee. You’ll instinctively reach for your Celine loafers when you want to add polish. You’ll layer your signature Byredo scent (Mojave Ghost or Eyes Closed, perhaps?) like the final brushstroke on a canvas.
You’ll stop shopping aimlessly. You’ll buy less, but better. And you’ll dress for you, not for the feed.
How to Embrace Style Trial & Error
Shop outside your algorithm
Don’t rely on your social media feed to tell you what’s stylish. Go to independent boutiques, thrift stores, or just observe people on the street. Let real-life texture inspire you.
Photograph your outfits regularly
This isn’t about perfection. It’s about seeing what actually works on you. Over time, you’ll notice patterns—certain silhouettes, lengths, tones that flatter and feel right.
Wear the “maybe” item anyway
That dress you’re unsure about? Style it three ways and wear it out. A maybe often becomes a favorite once it’s lived in.
Create a “Why Did I Buy This?” folder
Screenshot or list the purchases you regret. Analyze them. Was it peer pressure? A bad fit? Fabric that didn’t breathe? These lessons are gold.
Revisit the pieces you almost gave away
Styling ideas evolve. A skirt you once thought was “too much” might now fit your mood exactly when paired with a crisp oversized shirt from Studio Nicholson.
Confidence > Correctness
There’s no single “correct” way to dress. And the pursuit of that perfect, flawless outfit will often leave you uninspired. Instead, choose confidence. Choose curiosity. Choose motion over stagnation.
Style is a language—and every mispronounced word, every clumsy metaphor, every bold sentence makes your voice more unique. So wear the thing that might be “too much.” Try the shoe you don’t quite understand yet. Buy the jacket you can’t stop thinking about, even if it feels out of your comfort zone.
Because in the end, it’s not about being stylish by someone else’s standards. It’s about discovering your own—and letting the world see you through it.
So yes, style “mistakes” are a good thing. In fact, they might just be the best thing you ever wear.
