This is going to be an extremely vulnerable and personal reveal. I wasn’t going to share, since it doesn’t seem directly relevant to work fulfillment until it hit me that of course my personal experience has everything to do with the professional, since that is what I believe and teach in everything that I do. In my experience, our life and work are completely intertwined. Who we are at our essence and how we show up in every environment is deeply related and can’t be separated apart, as much as we might try.

I lived in Manhattan for many years and worked in the corporate world. You’ve probably heard that old adage “dress the part” which suggests you should wear the appropriate clothes for the life you want to have and the person you wish to be (perceived as). In my case (and perhaps you can related), this meant wearing corporate suiting for the executive suite to signal through your wardrobe your aspiration to achieve more and rise to a higher rung of the ladder.

The idea was to look the part as much as possible so others would already perceive you as “belonging” in that role. And of course clothing is a huge signifier. And you can see the many subtle and obvious ways this plays out in people’s beliefs and expectations. You just need to cue that infamous meeting with the current administration criticizing the Ukrainian President Zelensky’s military garb as not being serious or professional enough for a world leader (regardless of his country’s being at war).

And this plays out in other ways as style shifts and impacts what is considered power dressing now a days. If you never thought about how fashion and politics interconnect, you might want to reconsider after reading this summary of how fashion trends have shifted recently, why and how.

Since everyone in my family had their own business, none worked in the corporate world and I had no role models for how to dress corporate or what that even meant. As it was, I grew up around preppy boat culture and grew to detest khakis, polo shirts and boating shoes. It just wasn’t my thing. Not just because those clothes were never particularly flattering to my figure, but because I struggled to relate to or identify with that sort of drab beige uniform attire (Lily Pulitzer acid colors notwithstanding). Of course my Dad had every color of every shirt and Sebago shoe imaginable and had his own image of what constituted appropriate attire.

Needless to say my ambivalence around clothing began early. When I first began a bank management training program, I wore skirt suits in varying shades of grey and black. Then I evolved into pants suits which were much more comfortable. I wore high heels because height and power were closely correlated, and were the woman’s tie equivalent of dressing up for work regardless of how painful or impractical they were.

It’s no understatement that I used clothing as armor to try to fit in and look like I belonged. It wasn’t until leaving corporate to start my own business that I finally felt able to dress more like myself in outfits that I felt were professional and appropriate, yet still expressed my unique personal creative style. But the joke was on me.

I’ll never forget a former boss and “mentor” who I met with to explore business referral opportunities. I asked if she would introduce me to leaders within a different division of the bank where I’d worked for over a decade. She looked me straight in the eye and basically said she wouldn’t introduce me unless I changed my style and that I needed to pull back my hair and wear a more corporate “suit”. I told her that most of the startup founders I worked with wore jeans and sneakers. But clearly my cashmere sweater, skirt and boots were obviously not “suitable” or worthy of an introduction despite our years of working together and her familiarity with my experience, skills and contribution.

That experience stuck with me, (it’s been almost 12 years since that conversation). And of course, on some level, she was right. The SEVP of a major bank wearing Chanel and St. John was unlikely to take someone perceived as too casual and not professional enough seriously to support their business. In my head I told my former boss to fuck off and never followed up – with her or that organization.

Now maybe I was foolish and stubborn, never a good combination. Or perhaps I decided to put a stake in the ground after years of selling myself out, determining “enough, no more, I’m done conforming.” In my defense, multiple discussions over more than a year with another division of that bank never amounted to anything and it wasn’t exactly the work I wanted to do, so that validated my decision to walk away and not look back.

Now, should I have sucked it up, put on some pinstripes and heels with a fancy handbag and pimped myself out to get a meeting? Possibly. Arguably that would have been a smart move to get more business. What’s the big deal you might think? Sometimes it makes sense to do whatever is needed to win the job or land the meeting, especially when it’s not too much of a sacrifice. So, you wear a different outfit, you style yourself a little differently, you know “zhoozh things up a bit.” And clothes are just some schmattas after all, like icing on a cake.

There is that expression “putting lipstick on the pig” after all. But to me, the issue was much bigger. It was a turning point to not be at the mercy of this former boss who never saw me or my capabilities and who had very different ideas of what was possible. While she could have encouraged and supported me in my individuality, she felt a need to school me on the importance of conformity.

And she was potentially right if I wanted to stay where I had been and follow the rules she lived by. I knew that I needed to chart a different path.

I’ve been reflecting on this story as one of many as I explore my personal style. Our relationship to clothing and personal objects is so powerful. For some people, what they wear is purely functional, not particularly important or tied to their identity in any way. And if that was your experience, I’d be interested in hearing your perspective because I wonder if there’s some powerful insight there around awareness or privilege.

Yet for me, and arguably many women, people of color or those from different cultural backgrounds, abilities or body sizes and shapes, dressing the part and fitting in is fraught. It can come at a cost beyond clothing; that also has to do with identity and belonging.

Are we willing to sacrifice who we are in pursuit of our larger goals?

Sometimes we may need to make compromises – to “go along to get along” as one of my friends says – to achieve our objectives. But we also need to recognize when the cost of betraying ourselves is too big a price to pay. For instance, to realize when we’re working in a culture that doesn’t respect who we are, our values or unique perspective. Or when we report to leaders who don’t see or value our strengths and skills, or going along with certain “accepted” behaviors takes us away from what care about or believe in.

It’s important to consider these questions. Now you might think fashion is frivolous, but I’d argue that’s not really what this is about. I used to value being suited and booted, since it was how I prepared myself to show up for battle every day. To perform in roles that required me to win at all costs. Corporate profits entail a war with competitors and personal advancement often requires fighting others to get to and stay at the top.

While I dramatize for effect, that was my lived experience. And I saw it play out in so many ways. Companies that wouldn’t hire you back after you left, since you were a traitor or turncoat or executives who used to pit their direct reports against each other to see who would win out. Those cut throat strategies may have a place, and sadly they do help some leaders and organizations to get ahead. But at what cost?

I’m curious if you’ve ever considered whether the ways you dress have helped or harmed you? Which uniform, armor or war paint do you wear to battle in the world? What price have you paid for having to protect yourself in this way? Clothing is a form of armament and covering that signals rank, status, culture, and identity, for better or for worse.

Our clothes can also be tools in service of bigger goals, like standing out from the crowd or signifying political affiliations (think suffragists in white dresses or pink pussy hats and other signifiers). I’m no stylist or fashion historian, but our external representation can be deeply symbolic.

We’re all just naked human beings underneath everything yet think how much focus we put on wearing the right things. Those with kids (and many adults) know how obsessed we can become with buying and wearing the “right” brands (whether for cars, phones or other objects). That’s our marketing culture for you – homing in on our insecurities to make us buy more and solve problems that we don’t actually have until they made us aware what we should worry about.

Reflecting on my personal style has become much more fascinating than I anticipated, and this note has just touched the surface of how we judge others and ourselves around whether we measure up. As I journey to reclaim my truth, I’ve seen how my attire reflects so much more than it seems on the surface as it expresses my creative inspiration, travels, ideas and perspective on the world.

I’m so curious if anything that I’ve shared resonates and would love to hear what this brings up for you. If you’ve been wondering how you can feel more like yourself on both the inside and the outside, let’s connect. This deep and powerful work is the path to wholeness, integration and balance. I’d love to hear more about where these challenges around fitting in or changing yourself to feel that you belong play out in your world.

If you’re interested in how this relates to your leadership, check out my Leadership Default Codes assessment. Click here to take the quiz (5 minutes).

To being yourself,

Lenore

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