When did personal style become so…much….more?

I know the answer, and I’ll explain it here. Ok?

I’ll start with an analogy here. Stay with me, it will all connect.

Have you ever craved to learn a sport? Like tennis, perhaps. It looks fun, it’s an activity that will make you stronger, healthier and you can do it with others. All good. And you start, you buy the racket, you begin to understand the rules - the definition of “love,” the purpose of a baseline and net. Next comes a few lessons, learning how to use your racket, bring it back, follow through. Eventually you move on to understanding the perils of no-man‘s land and why it’s important for your feet to always be moving. You’re very focused on the mechanics, bring the racket back and low, follow through, reposition. And with much practice, you’re adding on - volleying, using topspin. Sometimes you nail the shot and other times it’s just about getting the ball in play. And often, especially in the beginning, there are moments or days when everything feels off, you’re choking and you don’t know exactly why.

Until you do.

Maybe you’re not playing with the ease that flows out of Jannik Sinner (I’m in italy at the moment, hence the choice), but never the less, your game is now playing with a natural reflex. You’re intuiting your next moves, when mistakes are made you’re not left fully bewildered. You know what you need to work on, you can trace back to what went wrong.

I see over and over people going through this same progression with their personal style. Like a good comedian, I don’t have to explain the joke here. I’m sure you can run this analogy through your head, just replacing key words above with personal style, clothing and getting dressed.

But here’s an unexpected outcome….

A phenomenon, if you will, that has played out in real time. Just like playing a sport makes you physically stronger, and healthier, strengthening your personal style has similar and far reaching consequences. Not because of a better image in the mirror, if it were that simple anyone who simply looks good would be incredibly competent, stable and a high achiever. It’s about the critical thinking muscle that’s been strengthened through the act of getting dressed each day with intent.

It was just around five years ago that I started talking about personal style in social media. This was foreign ground for me, I was forced in to going on line, it’s a long story, but I’ve no regrets. I began deciphering how to discover the codes of your style by thinking deeply about when it is you feel your best, when it is that your shoulders relax and you just “are”. The principles I created were built as guardrails, not an endeavor to re-write the rules of fashion but rather just a tracing back of when it was that I simply felt most at ease. Having lived in Asia, marrying a European and working with a veritable UN delegation of an office team, I’m acutely aware that my black may be your white. Decoding style and the words we use, like ease, wasn’t straight forward to visualize, ease can sometimes connote a sweatpant, a trainer, a lived in tee. But for me, ease meant the erasure of a sense of anxiousness and of second guessing oneself. It’s not the bold sense of confidence that you’re always right, but rather the sensation that you’ll figure it out. Somehow.

And there in lies the challenge. Because getting to this point takes practice, everyday in your closet. Not mixing and matching, but really thinking. It starts with something as simple as “how do I want to feel today?” But as many of you know, this quickly moves to curiosity - “hmmm, why do I crave to feel like this today?” It may come as a surprise that enroute to just dressing “more like yourself” you start understanding yourself better. And importantly, you’re putting words and visuals to it.

The ability to explain ourselves, to ourselves, can’t help but spill over in to other areas of our lives. The act of engaging in this discourse, daily, has had the following outcome for many:

• The more you understand your rationale for the choices you make, the more you believe that others have their own set of rationale for the choices they make.

• The more you can defend, if to no one but yourself, why you’ve made the choices you’ve made, the less anxious you feel when someone offers a contrarian point of view. It starts with articulating why you want that jacket tied around your waist; but just like the swinging of a racket, it soon becomes a natural muscle reflex. It’s not an understatement to say that when we understand the purpose behind our actions, we feel settled. And that tone, that calm, comes out in when you defend your choices without a sense of defensiveness. Try it. I promise.

• The more you recognize that something is “off” when getting dressed, and you’re empowered with the tools to compartmentalize the issues and problem solve, the more you crave to do this in your real life. Problems at work, at home, while on the surface different [this dress makes me feel too “pretty”] for example, mirror the approach we take in real life to move through discourse for results: identify the pain point, hypothesize the desired outcome [Edgier? Masculine? Grungier?], and experiment and test to see which path gets you there. I see in my real world all the time, things break down when we know there is an issue, but we aren’t 100% sure of the desired outcome and that ambiguity can spiral to inaction.

Somewhere along the way to finding and implementing my own personal style, my discourse got stronger. My head got held higher while my shoulders relaxed. Not because I looked great, but somehow I was just thinking clearer. I was curious, did a navy suit do all this? Did that strong shoulder give me the assurance that if things aren’t always right, I’ll figure it out, somehow? No. It’s much more nuanced than that. Or it was, until I figured I traced the last few years backwards.

If you’re reading this nodding throughout, I’m so happy for you. When you mention it to others, they probably look like you’re crazy, I feel your pain. If you’re sort of there, you’re reading this with hope and excitement. And if you just popped on here because you’re just out scrolling, you probably think I’ve lost my mind. And that’s ok. Because in actuality, I’ve found it.