7 fashion risks only bold, self-assured people take

We all know someone who can walk into a room and command attention—not because of designer labels or perfect styling, but because of how unapologetically themselves they are.

Fashion, at its best, isn’t about following trends—it’s about self-expression, courage, and confidence.

And while many of us play it safe with neutral colors and predictable cuts, bold people take chances.

The truth? These risks aren’t really about clothes at all. They’re about mindset, presence, and owning who you are.

Let’s talk about seven risks in style that only the self-assured truly embrace—and what they can teach us about confidence in life.

1. Wearing what feels right, even when it’s not “in”

Have you ever reached for something you love—maybe an old vintage coat, bold heels, or a quirky scarf—only to hesitate because it’s not what’s trending?

Confident people don’t pause. They wear it anyway.

As the American Confidence Institute reminds us, “Confidence is the best outfit. Feeling comfortable in your own skin at any age makes you appear more attractive.”

It’s not about whether Vogue approves. It’s about how alive you feel in your choices. When you embrace that, people notice—and respect it.

2. Mixing patterns, textures, and “clashing” colors

Most of us were taught to match. Safe combos. Predictable harmony.

But bold people aren’t afraid to throw stripes over florals or pair leather with lace.

I remember once layering a patterned kimono over a polka-dot dress for a dinner party. My first instinct was, “Tina, this makes no sense.” But when I looked in the mirror, I couldn’t help but smile—it felt playful, daring, and fun.

Sure enough, I got compliments—not because the outfit was “perfect,” but because it was fearless.

And as James Clear has said, “Every action you take is a vote for the type of person you wish to become.” Sometimes, choosing fearless patterns is casting a vote for a fearless you.

3. Ditching age rules and fashion “shoulds”

I’ve lost count of how many times women in my practice have told me, “I’m too old for that.”

But let’s pause—too old for ripped jeans? For bold lipstick? For sneakers with dresses? Says who?

Age rules are social constructs. Confidence is timeless. And I’ve noticed the people who radiate self-assurance often dress in ways that delight them—not ways that check boxes on someone else’s list.

It reminds me of a favorite Einstein quote: “Imagination is more important than knowledge. For knowledge is limited…Imagination embraces the entire world.”

Dressing with imagination instead of restriction? That’s a fashion risk worth taking.

4. Turning flaws into features

Here’s something I’ve seen again and again: confident people don’t hide what makes them unique. They highlight it.

Maybe it’s gray hair embraced proudly instead of dyed away. Maybe it’s a scar, freckles, or even a “flaw” turned into a signature look.

When I first started speaking at workshops, I was very aware of my slightly raspy voice. For years, I tried to downplay it. Eventually, though, I leaned into it—using it as part of my storytelling style. And you know what? People told me it made me memorable.

That’s the thing about authenticity: what you hide can weigh you down, but what you flaunt can make you magnetic.

5. Wearing statement pieces that spark conversation

Big jewelry. Oversized hats. A neon handbag.

These are not choices for the faint of heart. They say, “I’m willing to be seen.”

I once worked with a client who always wore bold, chunky necklaces. She admitted she was shy in conversation, but her jewelry gave people an easy way to approach her. Suddenly, she wasn’t the quiet woman in the corner—she was the woman with the unforgettable accessories.

It reminds me of something Brené Brown often teaches: vulnerability and visibility go hand in hand.

Putting yourself out there, whether through words or wardrobe, is how people connect with you.

6. Bending rules and creating your own

This one runs deeper than clothes.

The boldest people don’t just break fashion rules—they break life rules. They experiment, pivot, and resist the urge to fit neatly into a box.

Reading Rudá Iandê’s book Laughing in the Face of Chaos recently reminded me of this. He wrote, “When we let go of the need to be perfect, we free ourselves to live fully—embracing the mess, complexity, and richness of a life that’s delightfully real.”

That line stopped me in my tracks. Because isn’t that what bold style is about too? The refusal to be perfect, polished, or palatable—and the willingness to show up as your full, messy, wonderful self.

His insights inspired me to see my own wardrobe differently. Suddenly, fashion wasn’t just self-presentation. It was self-acceptance.

7. Wearing confidence louder than the clothes themselves

The boldest risk is realizing the clothes don’t actually matter. What matters is how you wear yourself.

I’ve sat across from countless clients who told me they bought “the right outfit” but still felt invisible. The truth is, your energy is the real statement piece.

Stand tall. Own your space. Make eye contact. When you radiate assurance, even the simplest outfit becomes unforgettable.

As poet Robert Frost once wrote, “Freedom lies in being bold.”

Final thoughts

Fashion risks aren’t really about hemlines or handbags. They’re about courage.

The courage to be seen. To ignore rules that were never really meant for you. To make mistakes. To experiment.

And most importantly—to enjoy the process.

So the next time you find yourself hesitating in front of your closet, ask: “Am I dressing to blend in—or to be me?”

Because when you choose you, people notice. And that’s the kind of confidence that never goes out of style.