As A Professional Closet Organizer, This is Why Most Closet Clean-Outs Fail

Photo Credit:@Stephanie Backer

Let me say this first, because it matters.

Most women do not struggle with cleaning out their closet.

They struggle with deciding who they are dressing for.

Most “how to clean out your closet” advice skips the hardest part — making confident decisions about what actually belongs in your wardrobe now.

I’ve been on all sides of fashion. I went to school for fashion design. I worked as a personal stylist. And now, as a fashion editor, I see how women interact with their wardrobes when there’s no mirror talk or Instagram pressure involved.

And the biggest issue I see, over and over again, is this:

Women dress for an older version of themselves.

Or an outdated one.

Or a version they think they should still be.

That’s why getting rid of clothes feels hard. It’s not about the clothes. It’s about letting go of an identity that no longer fits.

This is the exact process I use with clients when we clean out a closet together.

No hanger tricks. No minimalism guilt. Just clarity.

Tired of losing track of what you own? Download the free wardrobe inventory spreadsheet!

Step One: Identify Who You’re Actually Dressing For

Before you touch a single hanger, you need to pause.

This is why so many closet clean outs stall halfway through — you’re trying to organize clothes without redefining who they’re for.

Ask yourself:

• Where am I in my life right now?

• Does how I dress reflect that?

• Or am I dressing for who I used to be?

This step is everything.

A lot of women keep clothes because they represent a past season. A different body. A different job. A different lifestyle. And subconsciously, letting go of those clothes feels like admitting that chapter is over.

But here’s the truth:

Your clothes should support your current life, not archive your past.

There’s also something deeper happening here, and it’s real.

There’s a concept called enclothed cognition. It simply means that what you wear affects how you feel, how you behave, and how you show up. We all know this intuitively. You can wake up in a bad mood, shower, put on fresh clothes, and suddenly feel more like yourself again.

So if your closet is full of clothes that don’t reflect who you are now, getting dressed will always feel heavy.

This step isn’t about judgment.

It’s about alignment.

Step Two: Identify Who You’re Actually Dressing For

Once you’re clear on where you are, the next question is:

Where are you going?

Style goals matter more than most people realize. They’re not about trends. They’re about showing up for the life you want.

Think about the next six months.

• Are you aiming for a career shift?

• A promotion?

• Dating?

• Building confidence again?

• Simply wanting to feel pulled together instead of rushed?

Your clothes need to support that.

I think about this all the time when I’m out in the world. I once read a review for a coffee shop that said, “The place is beautiful, but it looks like the baristas rolled out of bed.”

And I felt that.

I’ve also been to a stunning, all-pink café where the space was dreamy, but the staff wore hoodies and sweatpants. It broke the illusion. The aesthetic didn’t match the energy.

This isn’t about judgment. It’s about presence.

When I worked in retail, we wore all black. A black turtleneck, black jeans, black boots. No effort, but instantly polished. That’s a style uniform. Steve Jobs understood this perfectly.

Style goals help you decide what belongs in your closet and what doesn’t. If an item doesn’t support where you’re going, it’s taking up space meant for something that will.

Step Three: Audit Your Lifestyle, Not Your Aspirations

This is where most people go wrong.

They shop for the life they imagine, not the one they live.

​​A true wardrobe audit looks at how you live Monday through Sunday, not how you wish you dressed once a month.

So before you start purging, look at your real week:

• What do you wear Monday through Friday?

• Are you at a desk?

• Running errands?

• In a uniform?

• Working from home?

• On your feet all day?

Then look at weekends. Travel. Events. Social plans.

A functional wardrobe has both:

• everyday, repeatable pieces

• a few aspirational items that make you feel excited

But if your closet is 80% aspirational and 20% practical, you’ll always feel like you have nothing to wear.

When cleaning out your closet, every item should answer at least one of these questions:

• Does this fit my current lifestyle?

• Does this support my style goals?

• Do I actually enjoy how I feel wearing it?

If the answer is no across the board, it’s not serving you.

Step Four:Decide What Stays Based on Fit, Feeling, and Function

This is the part people rush through, and it’s the most important.

I’ll give you a personal example.

After I gave birth to my son, I lived in sweatpants. Pink ones. Brown ones. Neutral ones. I had every variation. And for a while, that made sense.

But eventually, I noticed something.

When I took my daughter to school or ran errands, I didn’t like how I felt. Internally, it didn’t align with who I was becoming.

So I didn’t ban sweatpants. I evolved them.

I still wear them, but now I gravitate toward wide-leg styles that feel intentional. My Aritzia pairs work with boots. They feel styled, not sloppy.

Same with graphic tees. I love them, but once the neckline starts to stretch or fray, it changes the entire message. If I tell someone I’m a fashion editor and my shirt looks tired, the outfit speaks louder than my words.

These details matter.

Step Five: Decide What Stays Based on Fit, Feeling, and Function

This is where my system becomes non-negotiable.

We created the Wardrobe Inventory Spreadsheet in 2023 because memory is unreliable. Feelings are unreliable. Data isn’t.

Here’s how I use it:

• I spend a weekend logging the items I’m keeping

• I note categories, frequency, lifestyle use

• The spreadsheet analyzes patterns I wouldn’t see otherwis
  

It shows:

• how casual or dressy my wardrobe actually is

• where I have duplicates

• where I’m missing core pieces

• my dominant style patterns

This step turns a chaotic closet into information. And once you understand your wardrobe, shopping becomes intentional instead of emotional.

What a Closet Clean Out Should Actually Do for Your Life

It’s not to own less.

It’s not to be minimalist.

It’s not to have an aesthetic closet photo.

The goal is to:

• trust your wardrobe

• get dressed without stress

• stop buying random pieces

• feel like your clothes support your life

That’s what a stylist does. We don’t force decisions. We guide them.

And once you approach your closet this way, cleaning it out stops feeling overwhelming — and starts feeling empowering.

Tired of losing track of what you own? Download the free wardrobe inventory spreadsheet!