The Real Reason Getting Dressed Feels Hard

The Real Reason Getting Dressed Feels Hard

It Didn't Happen All at Once

You know, it doesn't all happen at once, eh?
It's not like one day you walk into your closet thinking you have to burn everything and start from scratch.

First you move for the first time — out of college and into your first apartment. Going through your clothes, you don't have much, but you leave behind a few things, ready to start your new life.

Then you get your first promotion, or at least go up for your first promotion, and you pick up a few pieces to help you in this new role.

Then it's a wedding you got invited to. You order a few dresses and one or two — or three — didn't make it back into the returns.

You went shopping with friends and picked up that new top that you weren't 100% convinced on, but your best friend said it looked amazing and you figured, for $48.99, what could it hurt to have it in your life?

Your mum gave you a sweater that's kind of itchy.

You bought a pair of jeans that became your entire personality for a summer.

You found this crazy vintage shop when you were in Italy on holiday.

And now you're standing in front of your wardrobe thinking, "I have nothing to wear."

It's not because you don't have a style. It's because no one taught you how to tie all of these memories together.

The internet would have you believe you're shopping this season for this season. Everything out — time to start fresh and make it cohesive! Maaaaaybe you can keep a few of the classics. Like the denim jacket or the jeans.

But that's not reality.

Reality is that I'm a professional personal stylist and I'm sitting here in Ottawa on a rainy day in a hoodie that belonged to my ex-boyfriend and a pair of joggers I picked up at a local thrift store.

Does it "work" as an outfit? No. You won't catch the visuals of this look on the internet anytime soon, but it works for right now, writing on my couch.

Because like your wardrobe, you're not a one-dimensional person.

We need clothes for our everyday life, and we need clothes that we love — and more importantly, we need the education on how to put them together.

So when you're standing in front of your wardrobe next time thinking, "I hate everything, I have nothing to wear" — just remember that's not true. The pieces you have in there are memories, stories, gifts, and probably a few things you could let go of, but they're there for a reason.

Something is tying those styles together, and that's what we're going to talk about next.


Your Style Theory: The Foundation of Getting Dressed


When you look at your wardrobe as a whole, what element stands out to you most?
Colour Print Texture Shape Details

Mentally, put them in order from most important to least important. I've worked with clients who have gone so far as to say, "hate."

Colour and print are the easiest ones to identify, but often this means you're missing connector pieces in your closet — things that feel "boring," like a white t-shirt or a denim jacket.

Details are another one that gets people saying, "this is so boring" when they're looking for things to match. It's not that the garment is boring — it's a supporting piece to the main character.

If shapes are your thing, you probably find it hard to layer. And textures can sometimes feel overstimulating on an off day.

But now that you have your theory, let's think about your aesthetic.


Your Aesthetic: What People Call 'Style'


This is what people generally call their "style."

Boho Edgy Vintage Chic

All of those are aesthetics.

The problem shows up when people don't want to say their aesthetic out loud. Things like:
Frumpy Grunge Basic

If you don't want to say it out loud, it's probably time for a change.


Your Gender Lean: The Element Everyone Forgets


The next thing to look at is your gender lean. Everyone has one, and your birth gender has nothing to do with it.

A masculine lean means you prefer more masculine elements — things like collars, ties, and structured pieces like trousers or jackets.

A feminine lean means you prefer more feminine elements — soft curves, a waist anchor point, and classically feminine shapes.

Once you mix all three together — your theory, your aesthetic, and your gender lean — you'll be able to get dressed in the mornings with little to no challenge.

What you'll notice is that the garment itself will change depending on the task in front of you. The theory you resonate with, the aesthetic, and the gender lean will all stay the same.


Ready to Go Deeper?
Now, I know this is a lot for a blog post — and that's exactly why I've put together a three-day immersive retreat for May 2026. If you want to really get a handle on your personal style and go shopping with a personal stylist to fill in the gaps, the link is below.

Learn About the Mother's Day Style Retreat


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