The NYC subway system is an excellent location for people watching.  Last week, during one of my midday commutes, a striking woman got on the subway wearing a hat you couldn’t miss.  It was a large felted style that had a plume of ostrich feathers, brooches, and other baubles attached.  It was fabulous, and a style this woman likely created herself.  Worn with this hat, this woman, who I’d say was in her early 60s and wore around a size 14-16, had on a cropped black leather moto jacket, an African-inspired printed midi-skirt, round sunglasses with purple lenses, and a few bold silver rings on her fingers.  

Even though our styles couldn’t be more opposite, and in a million years I wouldn’t wear anything she was wearing, I thought, “this woman knows who she is and she owns it.  She’s fabulous.”  

To give you context, I was wearing a navy blazer over a crisp blue and white striped button down, buttoned low and worn my preferred way— unkempt a bit, cuffs not buttoned, collar popped, like I am doing a walk of shame—worn over a white tank, slim straight jeans, a pair of mirrored penny loafers, and a classic orange Tod’s bag.

As I got up in preparation for my stop, this striking woman looked down at my mirrored loafers and mouthed, “I love your shoes.”  I took my AirPods out of my ears and returned the compliment, “I love your hat.”  After telling her where my shoes came from, we had a very quick —my stop is coming shortly — conversation.  I said, “I love your look,” to which she replied, “I love yours too.”  

It was clear from our conversation that we both were wearing what brought us joy and confidence.  “Life’s too short, right?” I said.  “Absolutely,” this woman agreed and said,  “People ask me where I am going in my hat, and my reply is always the same. ‘I don’t know, life?’”  I laughed in total agreement, wished her a great day, and got off at my stop.  

STYLE IS WHERE JOY AND CONFIDENCE INTERSECT

You wouldn’t be human if you didn’t, at some point in your life, think, “once X happens, I will be happy, and all will be okay.”  It could be about finally losing 20lbs., meeting a partner to share your life with, or getting a higher-paying job.  In psychological terms, it’s called the Arrival Fallacy, coined by Tal Ben-Shahar, which is a cognitive trap that has us believe that when we reach a certain milestone, we will have lasting happiness.   

In terms of overcoming the Arrival Fantasy, tips have often included things like learning to enjoy the journey, creating process-oriented goals that are fun to work towards, fostering appreciation for what seems small, and detaching from the end result.  

Going back to the encounter I had with the woman who would be a milliner’s dream, I thought about how we both were, as a result of leaning into what brings us joy to wear, how we engaged differently with the world, and likely with ourselves.  I thought, “Style is where joy and confidence intersect.  As far as the finished product is concerned, that’s entirely inconsequential.”  

What I mean by that is, here was this woman and I, with completely different styles, wearing clothing neither one of us would choose for ourselves, in utter appreciation of what the other was wearing.  It wasn’t about the clothing that mattered, but how each of us reflected ourselves back to the other.  The confidence and joy we cultivated made the journey of our lives a lot more fun.

DO YOU HAVE AN ARRIVAL FALLACY OF YOUR OWN STYLE?

 From a fashion perspective, so many women approach style like there is some magical point of arrival where they will finally become the woman who can “pull it off.” Once they lose the weight. Once they figure out their style. Once they become more confident. Once they have the right wardrobe, the right body, the right life, the right courage. Then they’ll wear the thing. Then they’ll take the chance. Then they’ll express themselves more fully.

Basically, women are waiting to become themselves before they allow themselves to become themselves.

The irony is that authenticity is often the thing that creates confidence in the first place.  When people are deeply comfortable in their authenticity, it changes how the world responds to them. Not because everyone suddenly loves their style, but because certainty is magnetic. Joy is magnetic. Self-possession changes social interactions.  The super cool woman in the hat probably gets constantly stared at. But she’s no longer dressing in anticipation of becoming herself someday. She already decided.  

WOMEN OFTEN APPROACH STYLE AS A DESTINATION PROBLEM INSTEAD OF A PARTICIPATION PROBLEM

Many women are waiting to feel confident before they participate in style, when confidence is often built through the participation itself.  Style is not a destination you reach where suddenly everything clicks into place, and you never feel unsure again. It’s not a finish line where a fully formed, perfectly dressed version of yourself is waiting with excellent posture and a capsule wardrobe.

Style is participation.

It’s trying the thing. Wearing the thing. Finding your favorite necklines.   Buying the bold glasses. Realizing you hate wide-leg pants. Discovering that, despite every fashion article insisting otherwise, you actually do look better in shorter jackets. It’s paying attention to what makes you feel more like yourself and what makes you feel like you’re wearing someone else’s life.

That woman on the subway in the feathered hat didn’t look like someone waiting to arrive. Neither did I in what I was wearing.  We both looked like women who had already decided to engage with ourselves honestly.

There’s a freedom in that.

CONFIDENCE DOESN’T COME AFTER YOU PERFECT YOUR STYLE

If you believe confidence is something that arrives after they figure style out, that once you finally have the right wardrobe, the right formula, the right body, the right trends, then you’ll be confident getting dressed, you’re coming from this backwards.

Confidence doesn’t magically appear after you perfect your style. It develops through the process of engaging with yourself honestly enough to discover what feels authentic in the first place.  You build confidence by experimenting. By getting it wrong sometimes. By trying things and realizing, “Nope, not me.” By also having those moments where you catch your reflection in a store window and think, “There I am.”

And that kind of confidence is far more durable than the confidence that comes from simply wearing what’s considered flattering, trendy, expensive, or correct.  True style confidence isn’t really about certainty. It’s about self-recognition.

The irony is, women often think they need confidence before they can wear whatever feels slightly outside their comfort zone. But most people who appear confident in their style didn’t start there. They became more confident because they kept participating in the process of becoming themselves.

In other words, confidence isn’t the prerequisite for personal style. It’s often the result of it.

AUTHENTICITY IS PRACTICED, NOT ACHIEVED

Authenticity is not some final state of enlightenment you eventually arrive at, as if one day you suddenly wake up fully formed, deeply self-aware, and completely immune to outside influence.  Authenticity usually develops much less dramatically than that. It’s practiced in small decisions over time.

Authenticity is noticing that you consistently feel better wearing some things over others. Things like structured jackets make you feel sharper and more like yourself. That despite trying to convince yourself otherwise, or that you hate fussy clothing, dry-clean-only fabrics, bohemian prints, sky-high heels, or whatever, simply doesn’t align with who you are.

Authenticity requires participation because you can’t discover yourself in theory. You discover yourself through interaction.

By trying things.
Rejecting things.
Returning things.
Loving things unexpectedly.
Feeling ridiculous sometimes.
Feeling amazing other times.

This is where women often get stuck. They believe authentic style should emerge perfectly and instantly, when in reality it’s usually built through years of paying attention to what consistently creates that feeling of recognition.  That woman on the subway likely didn’t wake up one morning and suddenly become “a woman who wears feathered hats.” She probably became her through a thousand tiny moments of self-recognition where she realized, “Yes, this feels like me.”

Authenticity isn’t achieved once and for all. It’s continuously practiced every time we choose to engage honestly with ourselves instead of dressing for approval, invisibility, or who we think we’re supposed to be.  Most importantly, it’s about trusting it.

LEARN TO ENJOY THE JOURNEY OF YOUR STYLE

Style is a journey, and it’s the points along the way that inform you. You have to try something once to know if it feels right, and often it’s those small hits of recognition that tell you where to go next.

At what point did I learn I loved blazers, or that I prefer to pop the collars of my crisp button-downs, or that jeans are where it’s at for me? By trying them and paying attention to how I felt wearing them.

And I think this is where many women get tripped up. They approach style as though they should somehow already know exactly who they are before they begin. They want certainty before experimentation. They want guarantees before participation. They want the final answer before they’ve even started gathering information about themselves.

But style doesn’t reveal itself all at once. It unfolds through experience:

Through the shirt you thought you’d love but never reach for.
The earrings you almost didn’t buy that suddenly become your signature.
The trend everyone swore you needed that makes you feel vaguely ridiculous.
The random jacket you throw on one day and unexpectedly feel more like yourself in.

Those moments matter because they create recognition.  And recognition is incredibly important in personal style because it’s often much quieter than people expect. It’s usually not some dramatic movie montage where angels sing and suddenly you’ve “found your look.” More often, it’s subtle. You catch your reflection walking past a store window and think, “Oh. There I am.”

That’s the journey.

Not arriving at some perfect final version of yourself, but collecting enough moments of recognition along the way that getting dressed starts to feel less like performance and more like self-expression.

IN THE END, WHAT YOU ACTUALLY WEAR DOESN’T MATTER AS MUCH AS HOW YOU WEAR IT

True style has very little to do with the specific items themselves. It’s not the what that people respond to most deeply. It’s the how.  It’s how fully someone inhabits what they’re wearing. How honestly they express themselves through it. How naturally their clothing feels connected to who they are instead of who they think they’re supposed to be.

That’s the part people overlook when they become hyper-focused on finding the perfect wardrobe, the perfect trends, the perfect formula, or the perfect aesthetic. They think style lives inside the clothing itself, when most of the magic actually comes from the relationship a person has with what they’re wearing.  This is why two women with completely opposite styles could look at each other across a subway car and feel immediate recognition.

Not because we wanted to become each other.
But because we both looked like ourselves.

NEED A HELPING HAND?

Just because style is a journey doesn’t mean you have to figure it all out alone. I know I’ve made this process sound simple, but for many women it isn’t. When you’ve spent years dressing for practicality, invisibility, approval, professionalism, trends, body changes, or simply getting through life, reconnecting with what actually feels authentic to you can take guidance.

And that’s okay.

Sometimes having someone help you recognize what’s already there makes the process a whole lot easier.

If you feel like you need a helping hand in discovering your own style, schedule a free Image & Style Assessment with me to learn how I can help you along the way.