How to Find Your Personal Style Again as an Adult

September 26, 2026

There’s something about back-to-school season that makes me nostalgic.

Maybe it’s the memories of carefully chosen first-day outfits, nervous anticipation and that strange feeling of standing on the edge of a new year, wondering who you might become.

I was walking past the local high school the other day just as classes were letting out, and it got me thinking about personal style and identity.

High school is such a funny time. You’re testing out identities, figuring out what you like, navigating new social dynamics and experimenting with a little more freedom. Clothing becomes part of that experimentation.

And then, somewhere along the way, many of us stop experimenting.

What happened to all that personality?

I was with a client recently when we somehow got onto the subject of teen fashion.

I remember getting ready for school very clearly. And, in stark contrast to what I saw walking out of the high school, sweatpants were absolutely not on the menu.

I probably would have faked an illness before willingly going to school in sweatpants.

How times change.

Last weekend, my daughter and I were sitting on the deck painting our nails. She enthusiastically chose a different colour for every single nail.

Ten nails. Ten colours.

She also loves big prints, pink and pretty much anything that can be described as a lot.

And the best part? The idea of what anyone else might think hasn’t really entered the equation yet.

It was a glorious contrast to the sea of mostly monochrome sweatpants and hoodies I had seen coming out of the high school.

Of course, our tastes change as we get older. And that’s a good thing.

We learn how to dress for different environments. We learn what feels appropriate for work, what makes sense for our lifestyle and what works for the role we’re stepping into.

But sometimes, in the process, we lose a little bit of ourselves in our clothes.

When your professional wardrobe becomes too safe

We all learn how to dress for the expectations around us.

Maybe it’s the office dress code.

Maybe it’s motherhood.

Maybe it’s a new leadership role.

Maybe it’s simply years of buying the things that seem like sensible choices.

Eventually, you can end up with the grown-woman version of teenage dressing to blend in.

The safe pants.

The bland cardigan.

The unremarkable top.

The perfectly acceptable outfit that does absolutely nothing for you.

And I’m not suggesting you show up to the office in rainbow nails, an orange leopard-print dress and a pink sweater. Although, frankly, I’m not opposed to any of those things individually.

The point is that professional doesn’t have to mean personality-free.

Your clothes can meet the expectations of your workplace while still giving people a little glimpse of who you are.

That’s part of what makes personal style personal.

How to rediscover your personal style

If you’ve found yourself stuck in a wardrobe full of perfectly reasonable clothes that don’t feel particularly you, start here.

1. Figure out what you actually like

Not what you think you should like.

If collared shirts aren’t your thing, you don’t need to build your professional wardrobe around them simply because someone once told you that successful women wear white button-downs.

If you hate them, you hate them.

There are plenty of ways to look polished and professional without wearing a collared shirt.

Take a more objective look at your wardrobe. What do you genuinely enjoy wearing? What do you consistently2. Start noticing what catches your eye

And no, this doesn’t have to mean creating a 47-board Pinterest obsession.

Just start paying attention.

What colours do you notice when you’re out?

What was it about that jacket that caught your eye?

Why do you love those earrings your colleague wore, even though you’ve told yourself you’d never wear anything like them?

What outfits do you find yourself looking at twice?

You don’t even need to buy anything.

Just notice.

Over time, you’ll start to see patterns. Maybe it’s colour. Maybe it’s interesting proportions. Maybe it’s texture, print, jewellery or a particular silhouette.

Those patterns are clues.

2. Start noticing what catches your eye

And no, this doesn’t have to mean creating a 47-board Pinterest obsession.

Just start paying attention.

What colours do you notice when you’re out?

What was it about that jacket that caught your eye?

Why do you love those earrings your colleague wore, even though you’ve told yourself you’d never wear anything like them?

What outfits do you find yourself looking at twice?

You don’t even need to buy anything.

Just notice.

Over time, you’ll start to see patterns. Maybe it’s colour. Maybe it’s interesting proportions. Maybe it’s texture, print, jewellery or a particular silhouette.

Those patterns are clues.

3. Make one small change

You don’t need a wardrobe overhaul to rediscover your personal style.

In fact, I’d argue that you probably shouldn’t start there.

Try adding a belt to an outfit you normally wouldn’t.

Change the shape of your trousers.

Swap your standard cardigan for a blazer. Or your blazer for something softer.

Wear the earrings.

Try the shoe you normally save for “going out.”

Take one of your usual outfit formulas and change just one element.

The goal isn’t to become someone else.

It’s to find out what happens when you give yourself a little more room to experiment.

4. Give yourself some grace

This might be the most important one.

You’re going to try things that don’t work.

Good.

That’s how you figure out what does work.

We can be remarkably critical of ourselves when it comes to getting dressed. And because we see ourselves every day, we often have a much more critical eye than anyone else does.

So take some swings.

Try something slightly outside your comfort zone.

You might hate it.

You might love it.

Either way, you’ve learned something.

Your personal style doesn’t have to be loud to be visible

Maybe rainbow nails aren’t your thing.

Maybe a little leopard is.

Maybe it’s a different shirt shape.

A great pair of earrings.

A more interesting trouser silhouette.

A colour you normally talk yourself out of.

A jacket with a bit more personality.

You don’t need to dress like a teenager to dress with personality. And you certainly don’t need to turn your wardrobe upside down.

Sometimes finding your personal style again is simply about giving yourself permission to notice what you like and make a few different choices.

Your clothes don’t need to shout.

But they should say something.

And preferably, they should sound a little bit like you.

Ready to figure out what that looks like in your own wardrobe? A closet edit can be a great place to start. Rather than adding more clothes, we can look at what you already own, identify what’s working, uncover what’s missing and build some new outfit formulas around you.

Because your closet may already contain far more personality than you think.

Personal Shopper Toronto, GTA, Pickering, Brooklin

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