You Should Care About Your Personal Style

I’m standing in front of a hundred executives wearing a fitted sheath dress and a statement necklace, because it is the early 2010s and of course I am.

“You have seven seconds to make a first impression,” I tell them.

I deliver the line with authority, pause for effect, and move to the next slide. The audience is paying attention. The presentation is underway. And I am already bored to death.

From about 2010 to 2017, a significant part of my work involved traveling around the country speaking to businesses and their employees. I liked the work for the most part. I enjoyed being in a room with people, hearing their questions, and seeing which parts of a presentation actually connected with them.

The content I was contractually obligated to deliver was another matter.

Almost every presentation began with that same seven-second line. And listen, there is truth in it. How we present ourselves affects how other people see us, especially in professional settings.

But dressing to create an impression has never been my thing. I have never been interested in helping women dress for an audience. I want you to dress for yourself. When you feel comfortable, confident, and recognizable to yourself, the impression you make tends to take care of itself.

The seven-second line was there to lend credibility to everything that followed. We had to establish that appearance affected professional success because that was the approved way to make clothing sound like a legitimate business topic.

I always found that fascinating. The people putting these programs together seemed to believe that we couldn’t simply talk about getting dressed, shopping, or how it feels to wear something you love. We had to talk about personal branding, executive presence, and managing perception.

I did what I could inside of that. I brought warmth into the room, made jokes, told stories about my own clients and my own mistakes, and worked to make an hour about clothing feel like a conversation rather than a training module. That part was mine.

But the framing was never negotiable. The companies were specific about the language they wanted, and I delivered it.

Once I got through the corporate language and opened the room to questions, the entire conversation would change.

Men and women alike wanted to talk about shopping. They wanted to know which brands were worth the money, how a jacket should fit, where to find pants for a difficult body type, and what they were supposed to wear to an event with an indecipherable dress code. They shared stories about things they loved, expensive mistakes hanging in their closets, and outfits that made them feel their best.

The questions were specific, personal, and usually far more interesting than the presentation.

Inevitably, there were a few naysayers in the crowd. And if I’m being honest, which I always am, they made me crazy.

I have very little patience for contrarianism for its own sake, particularly when someone stands up in a room full of interested people to announce that the subject being discussed doesn’t matter. But I also didn’t believe their resistance was always as simple as not caring about clothes.

I often wondered what was underneath it. Maybe they resented the idea that appearance affected how they were treated professionally. Maybe fashion had never made them feel welcome or represented. Maybe caring about clothes felt vain, financially irresponsible, or like one more expectation they had no interest in meeting. Maybe declaring that none of it mattered was easier than admitting that getting dressed had become frustrating.

I wanted to find the right way into that conversation. I wanted to explain that caring about personal style did not require chasing fashion, spending a lot of money, or dressing for someone else’s approval. I wanted them to see that clothing could be practical, creative, enjoyable, and entirely for themselves.

But that wasn’t my job in the moment. I was there to deliver a presentation, answer the questions I could, and help the people who had come ready to have the conversation. I couldn’t stop the room and try to change one person’s mind, even when part of me wanted to.

What I wanted to say to them, and to everyone else in the room, was much simpler than the presentation I had been hired to give: I want you to care about your personal style because you will feel better.

That is the whole agrument.

You will feel better when you open your closet and see clothes that fit your body and make sense for your life. You will feel better when you walk into a meeting without adjusting your sleeves or wondering whether you chose the wrong shoes. You will feel better when you can get dressed for dinner, a trip, or an ordinary Tuesday without trying on half your closet first.

You will feel better when you recognize yourself in what you’re wearing.

And when you feel good in your clothes, you can stop thinking about your clothes.

So much of the advice women receive about getting dressed is focused on the person looking at us. Dress for the job you want. Look younger. Look successful. Wear the right thing so people take you seriously. Avoid the wrong thing so they don’t make assumptions about you.

There are moments when that matters. Clothes communicate, whether we intend them to or not. A job interview, a major presentation, a wedding, and a funeral all come with expectations worth understanding.

But those moments make up a very small part of most women’s lives.

We also get dressed for school pickup, grocery stores, doctor’s appointments, workdays at home, casual dinners, and hours spent in the car. We get dressed for regular Tuesdays when no one is evaluating our executive presence or considering us for a promotion.

What we wear still affects those days.

You know the difference between wearing pants that fit comfortably and spending ten hours thinking about your waistband. You know how it feels to put on a jacket that brings an outfit together or to leave the house in something that never felt right and carry that discomfort with you.

You also know the relief of having an outfit ready when an invitation arrives instead of ordering six dresses and hoping one of them works.

None of this is life or death. But it is your life, and you are allowed to want this part of it to function better.

Women are expected to look good while pretending it required no effort. We are supposed to know what fits, understand changing dress codes, recognize which jeans feel current, and dress appropriately for our age without appearing to care very much about any of it.

If we admit that we enjoy clothes or want to feel attractive, we risk being seen as vain. If we say getting dressed has become difficult, we feel obligated to explain that we know there are more serious problems in the world.

Of course there are. Personal style is not the most important thing in my life, and I assume it isn’t the most important thing in yours.

It does not have to be.

You wear clothes every day. You spend money on them and give them space in your home. They can make your morning easier or create frustration before the day has properly started. Caring enough to make that part of your life work well is entirely reasonable.

You may also simply enjoy it.

You might love what happens when you put on a great jacket. You may notice the difference the right shoe makes or enjoy adding jewelry to something simple. You might find color, fabric, shape, and proportion genuinely interesting.

You don’t have to turn that interest into a lesson about confidence, productivity, or professional success before you’re allowed to have it.

For many women, getting dressed becomes harder with time. Their bodies change. Their jobs change, relocate, or end. Children arrive, grow up, or leave. Social lives and schedules shift. Dress codes become more casual and somehow more difficult to understand.

Their taste changes too, but their closets don’t necessarily change with it.

A closet can easily become a record of several past versions of your life. There are clothes from the office you no longer visit, dresses from a more formal calendar, and pieces purchased for a body that has changed. Meanwhile, the clothes required by your current life are limited or bought quickly because you needed something immediately.

That disconnect can make you think you have lost your personal style. More often, you are relying on rules and habits built for a woman with a different calendar.

Figuring out your style now means looking at three things: what you are drawn to, what your life requires, and what your own closet has already taught you.

Your favorite jacket is evidence. So are the shoes you wear constantly, the color you reach for in every store, and the print you repeatedly buy but never put on. The pieces you love and the purchases you regret have all been giving you information for years.

The work is organizing it into something you can use.

That is what we are doing during Personal Style Discovery Week exclusively on The Well Dressed Life.

This week, I’m walking readers through the process and conversations I used with private styling clients. We’re starting with why figuring out your personal style is worth your time. Then we’ll create a Personal Style Vision Board, map your wardrobe to your actual life, clear away some of the myths that make getting dressed harder, and bring everything together in a Personal Style Plan.

By the end of the week, you’ll have a clearer understanding of your style, and a much better filter for deciding what belongs in your closet and what deserves your money.

I want you to care about your personal style because you are the one living in your clothes.

And I want you to feel good there.