Are You Cringe? What Makes Something Cringe?
Adventures in self esteem, power and belonging
You just spent four figures at your favorite boutique—maybe a little more if you’re the kind of person who thinks espresso counts as a meal. You strutted out with your new treasures feeling like the main character in a European art film.
But now you’re in front of your bedroom mirror. Lights on. Makeup off.
And it’s giving cringe. Big time.
The color feels like it’s shouting.
The silhouette that screamed “seductive” in the dressing room now whispers “trying too hard” under your bathroom light.
What happened?
You fell into the oldest trap in fashion: confusing fantasy with reality.
It’s not your fault. The mirror at the store was tilted. The playlist was vibing. The sales associate told you you could pull it off. (Of course she did—she works on commission.)
This is a sensitive topic. One I’ve hesitated to share.
Judgment is the lazy route. But self-awareness? That’s where the good stuff lives.
Cringe—awkward embarrassment—is universal. Whether you overdo it or underdo it, you’ve felt it. In high-pressure social moments, and even the casual ones.
So here we go. I’ll be as unfiltered as possible, since that’s what helps the most.
The Trouble Starts with the Scroll
Let’s start with the portals of temptation: social media and shopping sites.
Getting you hyped about the latest trends—whether they suit you or not—is their entire business model. Intense colors, wild prints, naked dressing... These things have a time and place, especially if extroversion is your jam. They’re joyful, they’re attention-grabbing, they reflect life in all its drama.
Themed parties?
They exist purely so you can cosplay the one-off looks that don’t fit into your real life. It’s a full-circle cringe moment—hilariously orchestrated for laughs, joy, and a little performance art from the hidden corners of your personality.
But that’s not the real story here.
Low self-esteem comes in many forms—but in style, it often shows up as confusion.
We’re unclear about our motivations. We’re mired in shame.
So let me ask you:
Who are you trying to bond with?
What impression are you aiming for?
If you miss the mark, cringe may be on the menu.
Cringe Is a Compass
Let’s pause on the word itself.
“Cringe” is emotionally sticky—it’s the psychological equivalent of stepping in gum.
But it’s not all bad.
Cringe is a signal that your inner compass is still working.
You feel off because something is off.
And the good news? That’s fixable.
There are safe routes: tonal looks, matching sets, all white, all black, double denim, jeans and a tee. These are fail-safes. They assemble in a hurry. They work beautifully if you’re avoiding fashion drama and living a minimalist life.
But if you’re trying to express your actual point of view—your style DNA—those looks might fall short. Because minimalism doesn’t fix discomfort in your body.
When we dress to mask malaise without doing the inner work, we get two options: cringe or boredom.
What we want is flow—a style that feels effortless because it fits.
Money Helps, But Intuition Wins
Throwing money at your wardrobe can be fun.
It’s creative. It’s worth investing in. But the long-term upgrade?
Self-knowledge.
Learn what works for your body, your life, your mind. And your closet will start working for you.
If you're struggling, start here:
Study the natural shape of your body—and learn to love (or change!) what you see.
Play with balance and proportion for options beyond “classic.”
Hone your color palette and accessory game.
Keep it simple, sporty, tailored, and elegant for maximum impact.
Your Style Should Match Your Self-Image
Cringe happens when there’s a mismatch between how you see yourself and how you present yourself.
Often, it’s subconscious—until the mirror catches up.
Your wardrobe is your PR team.
And when your clothes pitch a version of you that doesn’t ring true, your body notices.
That tight feeling in your chest?
That impulse to change before anyone sees you?
That’s your brain whispering: Honey, this isn’t us.
Aspirational Mood Boards vs. Actual You
Social media has turned us all into walking mood boards.
The trends! The palettes! The leather bustiers at 11 a.m.!
If you click “add to cart” while imagining yourself as a cocktail-sipping, Vespa-riding Milanese heiress… pause.
That’s not styling. That’s daydreaming.
Lovely—but not helpful when you’re late to a dentist appointment and dressed like a statue.
Stylist’s trick: Ask yourself:
“Where am I actually wearing this?”
If the answer involves a fantasy scenario—not a real event on your calendar—you may be buying into someone else’s persona.
Bold Doesn’t Equal Believable
Loud prints and cutouts are glorious—if you’re wired for them.
But if you’re naturally low-key, retina-scorching chartreuse might make you feel like you’re in costume.
Here’s the rub: people can sense when you’re not at ease.
That’s where the cringe starts—not because the outfit is bad, but because it’s not yours.
Fashion is a stage.
Style is the script you know by heart.
Dress for the Room You’re In
Here’s a brutal truth from someone who’s seen models cry in couture:
Style is context-dependent.
What looks iconic at a Paris gallery opening can read as “midlife crisis” at a suburban Starbucks.
(No shade—I love their cake pops. But it’s not the Met Gala.)
Psych hack: If you often feel overdressed or underdressed, your cringe-o-meter is picking up a social mismatch.
Don’t dim your light to fit in—but do calibrate.
Think: Coco Chanel, reading the room.
Your Clothes Shouldn’t Apologize for You
Some people dress “extra” to distract from insecurity.
Others hide in beige to avoid attention.
Both are fashion self-sabotage.
You shouldn’t need sequins to feel interesting.
You shouldn’t need to disappear to be taken seriously.
Take up space. But do it in a way that reflects your values, lifestyle, and body.
Stylist’s trick: Ask yourself—
Do I feel more like myself in this?
Would I wear this if no one was watching?
Would I still like it if I saw it on someone else?
If the answer is “no,” take it off.
Return it. Sell it. Burn it in a ceremonial blaze if it helps.
Life’s too short to feel like a walking identity crisis.
Final Thought: You’re Not Cringe—You’re Evolving
Let me tell you something.
After 30 years in this business—with a front-row seat to everything from Naomi Campbell tantrums to interns crying over sample returns—I promise you:
Everyone feels cringe sometimes.
Even the icons.
Especially the icons.
That awkward feeling is a signal that your style is evolving—catching up to who you’ve become.
Fashion wants you to be trendy.
Style wants you to be honest.
So cringe a little. Then listen.
That discomfort? It’s the beginning of your real personal style.
You’re not alone in the cringe.
We’ve all been there—overdressed, underdressed, or just off.
But style is a practice, not a performance.
Subscribe for more tools, truth, and tough love—from someone who’s worn the mistakes so you don’t have to.
With love,
Lisa
Loved reading this! Quick q: when you say ‘calibrate,’ what exactly do you mean? I live in the Midwest and somehow still end up overdressed in just a button-down and jeans! 😭
Thank you, Rachel! So glad you enjoyed it!