Cool, Unscripted

October 18, 2026

Ink-and-wash illustration of a woman in a navy dress with white trim and white boots beside a red electric guitar, with the Bay Bridge in the background.

Jazz, white boots, and the business of being yourself
The Très Chic Edit | Culture, Fashion & The Business of Being Human

When a member of Jaz Force approached our table at Mersea, my first thought wasn’t particularly glamorous.

Does he need me to move?

He did not. He was introducing himself.

I had to laugh at how quickly I’d mistaken a friendly hello for a logistical problem. Here was someone making conversation with people enjoying the music. No pitch. No elaborate opening. Just a person saying hello.

I was wearing a mini dress and white pointed-toe boots with a modest half-inch heel. Dressed for an afternoon out, prepared for a little walking, apparently unprepared for an introduction.

Perhaps I had become too accustomed to introductions that wanted something.

The afternoon had started at the final Saturday of Off the Grid on Treasure Island. There were food trucks, drinks, lawn chairs, shaded tents, and people making the most of the California sunshine. There was also a dog runway show, because in San Francisco, even the dogs have somewhere to be and a look to deliver.

Overhead, kites moved through the sky. A vendor offered rentals, a reminder that an enjoyable afternoon could still be arranged with some string and a cooperative breeze.

Eventually, I wanted more shade and a proper seat. Mersea supplied both, along with fish and chips that justified the move: crisp batter, tender fish, excellent steak fries.

Then there was the music. Jaz Force was playing jazz and rhythm and blues, giving lunch the pleasant possibility of becoming the rest of the afternoon.

I had come to eat. I stayed because I liked being there.

Anyone who works in business should pay attention to that distinction.

An outfit can only do so much

I enjoy getting dressed. I like the decisions: the silhouette, the shoes, the detail that makes an outfit feel like mine. That afternoon, it was the white boots.

There was no larger strategy. I wasn’t dressing to establish credibility, signal membership, or become someone else’s idea of interesting. I wanted to wear them.

Fashion gives us that pleasure. It lets us express a mood before we’ve found the words for it. Sometimes it even helps us discover the mood.

But I would never ask a pair of boots to vouch for my character.

A beautifully dressed person can still be rude to the server. Someone with an impressive title can fail to keep a small promise. A carefully cultivated image may tell us how someone wants to be seen while revealing very little about what it is like to know them.

The outfit is an introduction. Eventually, we have to take over.

That was part of what I had been trying to get at in an earlier piece about trust, style, and professional credibility. I had the principles. Sitting at Mersea, I finally had the feeling.

The pleasure of an unplanned conversation

We spend a remarkable amount of time preparing to meet one another.

We refine introductions, work on our personal brands, study body language, and learn how to make an impression. Some of that is useful. Knowing how to listen or put someone at ease is worth the effort.

Still, there is something exhausting about approaching every room as an opportunity to position yourself.

At some point, someone has to stop managing the impression and join the conversation.

The musician’s introduction felt refreshing because it didn’t seem to require anything from us beyond a response. We were enjoying the band. He came over to say hello. The exchange was allowed to be as simple as that.

It reminded me how much I appreciate meeting people without immediately deciding what the meeting is for.

You can arrange a dinner, attend an event, or introduce two people you think might get along. You can create the occasion. You cannot supply the chemistry.

Anyone who has been on a promising date knows the difference.

There is no shortage of advice about becoming more likable. I’m more interested in what happens when we’re curious enough to find out whether we actually like one another.

That requires a little less performance. It also requires accepting that not every connection will become something.

A perfectly pleasant conversation is allowed to remain a perfectly pleasant conversation.

A little room to improvise

Listening to the band, I thought about the kind of individuality we associate with jazz: a recognizable voice, a willingness to experiment, the confidence to contribute something of your own.

But also the ability to listen.

That last part gets less attention in conversations about being original. We tend to picture the person commanding the room, not the person paying close enough attention to know when to come in.

There is a social lesson there, although I doubt the afternoon needed me to turn it into a seminar.

You can have a point of view without occupying every available inch of space. You can bring something distinctive without requiring everyone else to become your audience.

I’ve always been drawn to people who think independently. I’m also aware of how quickly a group that celebrates individuality can develop a very specific idea of what individuality should look like.

We welcome originality, right up until it arrives wearing the wrong thing or disagreeing with us.

I include myself in that scrutiny. It is easy to appreciate an independent mind when it confirms your own.

The more interesting test is whether we can stay curious when it doesn’t.

In my work in sales and operations, and in my studies in business and decision sciences, I’ve learned to value both conviction and the willingness to reconsider. Questioning a process is useful. Understanding why it exists is useful, too. If you want to improve it, eventually you need more than a persuasive objection.

You need evidence, persistence, and a workable alternative.

The same humility helps outside work. Having your own mind does not mean assuming everyone else has misplaced theirs.

The business behind a good afternoon

There was another reason Mersea stayed with me: the experience worked.

The food, the setting, the music, and the welcome supported one another. I didn’t need to be told I was having a good afternoon. I was having one.

That is harder to deliver than a good marketing line.

In sales, you can learn all the right questions and still fail to hear the answer. In branding, you can describe an exceptional experience that your operation is not equipped to provide. You can make a compelling promise and leave someone else to explain why it wasn’t kept.

My experience has made me fairly practical about this. A good sale begins with understanding what someone needs and deciding whether you can meet that need.

If you can, explain how. If you cannot, be honest about it.

Then make sure the rest of the experience supports what you said.

That includes the less glamorous work: accurate information, a product that matches its description, delivery, communication, and follow-through. The relationship may begin with the person making the introduction, but it depends on much more than that person’s charm.

You don’t have to force the customer to admire you. You have to give the customer a good reason to trust you.

I thought about that at Mersea because nobody appeared to be working quite so hard to win me over. The work was in what they delivered.

There is a difference.

Thank you for letting me be myself

Sitting there, I thought of Sly and the Family Stone’s “Thank You (Falettinme Be Mice Elf Agin).”

A fitting thought for an afternoon that had given me very little reason to be anyone else.

I’ve earned something of a reputation for insisting on being myself. I can question an established way of doing things, particularly when the rules seem to have wandered away from their original purpose.

I don’t think that makes me right every time. It does mean I want room to ask the question.

And I want to extend that room to other people.

Room to dress differently. To have an unfamiliar interest. To disagree without turning the exchange into a contest. To introduce themselves without delivering a polished explanation of why they are worth knowing.

The afternoon at Mersea offered a small, welcome version of that freedom. We could enjoy the food and the music. Someone could say hello. I could wear my boots.

Nothing needed to become a referendum on who belonged.

Perhaps that sounds like a modest ambition. Lately, I find modest pleasures increasingly persuasive.

Cool, without the campaign

At The Très Chic Edit, clothes are part of how I explore these questions, not a substitute for answering them.

I love a distinctive piece. I love the confidence of wearing something because it feels right to you. But the people I remember most are rarely memorable only for what they wore.

I remember whether they listened. Whether they were kind when kindness offered no obvious advantage. Whether I could relax around them.

That afternoon reminded me how good it feels when an encounter has a little room in it. Room for surprise, humor, or a conversation neither person could have planned.

So wear the boots. Order the fish and chips. Enjoy the band. Introduce yourself.

You can put thought into an outfit without planning the conversation.

Leave a little room for the unscripted.