Learning to Trust Your Own Taste

There is an entire industry built around telling people what to wear.

Fashion magazines. Influencers. Lifestyle websites. Social media algorithms. Every one of them promising some version of the same thing: buy these pieces, follow these rules, adopt these trends, and you will finally be stylish.

I’ve never completely connected with that. In fact, I’ve actively rejected it.

When I think about fashion, I think about runways, Fashion Week, celebrities on red carpets, and designer labels most people will never own. Fashion feels distant. It feels expensive. Sometimes it feels more like an art form than something connected to the realities of everyday life.

Style, on the other hand, is different.

Style is personal. It is how we choose to put ourselves out into the world. It is our personality, our preferences, our lifestyle, and our sense of self made visible. Fashion can influence style, but it cannot create it. Style happens when an individual takes those influences, distills them, and decides what belongs and what doesn’t.

That distinction took me a long time to understand.

Leaving the Uniform Behind

Looking back, I don’t think I spent much time thinking about style when I was younger.

Part of that was the era. I came of age during the grunge years. Torn jeans and flannels were everywhere, and I was right there with everybody else. Then came that strange swing music revival period when bowling shirts and black-and-white wingtip shoes somehow became fashionable again. I participated in that too. Looking at some of those photos today is enough to make me cringe a little.

But the bigger factor was my career.

For more than a decade, I worked in public safety. I wore a uniform every day. The decisions for my wardrobe had already been made for me. My clothing wasn’t an expression of identity. It was a requirement of the job.

When I eventually transitioned into professional life, everything changed. For the first time, clothing became a series of choices. What I was wearing wasn’t just about what was appropriate, but what felt right. What represented me. What made me feel confident. And I was delighted to discover that I genuinely enjoyed that process.

Not because I cared about trends.

Because I enjoyed figuring out who I was, and how I presented myself.

The Coat I Couldn’t Stop Thinking About

One of the clearest examples happened completely by accident.

Back in 2007, I was in London with a group of friends. There was a snowboard and skate shop next to the Tube station we used every day. Sitting in the window was a brown Burton winter coat that immediately grabbed my attention.

The problem was the price.

At the time, the exchange rate was brutal. One British pound was worth roughly two American dollars. Every time we walked past that shop, I stared at the coat. Every time we passed it again, I stared at it a little longer.

Eventually my friends got tired of listening to me talk about it.

“Just buy the damn thing already.”

So I did. And I loved that coat.

I wore it for years. Not one season. Not two seasons. More than a decade. It became one of those pieces that felt completely and undeniably mine.

Years later, while helping family with an estate sale, someone broke into the room where employees and family members were storing their personal belongings and stole it.

I still miss and think about that coat.

What strikes me now is that nobody had to convince me to like it. Nobody told me it was fashionable. Nobody posted a top ten list of coats to wear that winter season.

I saw it. I loved it. I bought it.

Sometimes style is that simple. Instinctual. Immediate.

The Problem With Clothing Gifts

One of the questions I was asked while thinking about this article was why I dislike receiving clothing as gifts.

The answer surprised me.

It’s because style is personal.

When somebody gives you a shirt, they’re making a guess about who you are. Sometimes they get it exactly right. Sometimes they miss completely.

The best example of someone getting it right happened during the pandemic. For my birthday, my family gave me a gift certificate to Boston Scally.

At the time, I had never heard of the company.

Their note said something along the lines of, “This feels like something you’d be into.”

They were right.

I bought my first scally cap. And now I own enough of them that we should probably stop counting.

What fascinates me about that gift isn’t the hat itself. It’s the fact that they recognized something about me before I recognized it myself.

That’s rare.

Most of the time, when somebody buys us clothing that doesn’t resonate, the reaction isn’t that the item is ugly or poorly made. The reaction is much simpler.

“This isn’t me.”

That’s what makes clothing such a difficult gift. Style sits very close to identity.

The Things We Keep

The older I get, the more I think personal style reveals itself through repetition.

Not in the things we buy, but in things we keep.

For decades I’ve owned an old Outback-style slouch hat that I originally bought in Florida. The kind with the wide brim and the snaps that let you fold up the sides.

I’ve had people compliment it. I’ve had people make fun of it. I’ve even had women ask me not to wear it.

I ignored all of them.

The hat is still in my closet.

For a period of my life, people practically associated me with it. If I was outdoors, I was wearing it. It went camping. It went to barbecues. It went to parks, beaches, and road trips.

It’s still here because it survived every attempt to convince me otherwise. And that tells me something.

Style isn’t always found in the things we acquire. Sometimes it’s revealed by the things we refuse to let go.

The Possum Shirt Test

Yesterday I found myself wondering whether anyone made a short-sleeve button-down shirt covered in possums.

That is an absurd sentence, but stay with me.

I love colorful, short-sleeve, button-down, Aloha-style summer shirts. Florals. Fruit patterns. Bright colors. They make me happy. Somewhere in the middle of that thought process, I wondered whether anyone had made a possum version.

Naturally, the internet provided options. Lots of options.

Possums dressed as pirates. Photo-realistic possums. Every possible variation you could imagine.

Then I saw one where cartoon possums were eating hot dogs, pizza, ice cream, and other summer cookout food. And my reaction was immediate.

“That’s the one.”

I didn’t need a review. I didn’t need validation. I didn’t need someone to explain why I should like it.

I just knew.

The more I thought about it, the more I realized that’s how most of my favorite clothing finds its way into my life.

It rarely requires a ton of thought or debate. Something clicks.

You see it. You recognize it. You trust the feeling. And you buy it.

Learning to Trust Yourself

I think this is what genuinely stylish people understand.

People often mistake confidence for style. The two are closely connected, but they aren’t the same thing. The confidence isn’t coming from the clothing itself. It’s coming from the certainty.

They know what they like.

They know what feels authentic.

They aren’t dressing according to somebody else’s expectations. They’re dressing according to their own.

And I’m not going to lie… that becomes easier with age.

Not because taste magically improves, but because you spend enough years experimenting to recognize your own patterns. You stop chasing approval. You stop trying to fit into categories that don’t feel natural. You become more comfortable trusting your own instincts.

The result isn’t necessarily a better wardrobe. It’s a more honest wardrobe.

You Already Know More Than You Think

People may often lament and say they don’t know what their style is.

I don’t think that’s true. I think most people simply haven’t learned how to recognize it.

The fact is your wardrobe already contains the evidence.

Look at what you wear immediately after it’s washed.
Look at the colors that appear over and over again.
Look at the items you’ve owned for years.
Look at the clothes that make you feel comfortable, confident, and completely yourself.
Then look at the things that sit in the back of your closet untouched.

The answers are already there.

Style is not about becoming somebody new. It is not about following trends. It is not about building a wardrobe that impresses strangers.

It is about paying attention because the clues have been there the entire time.

Learning to trust your own taste isn’t about becoming someone new.

It’s about recognizing what your style has been all along.

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