7 Questions to Declutter Your Closet

Are you looking for tips on how to declutter your closet? If so, you’re definitely not alone!

I’ve been a minimalist for nearly a decade and during that time, I’ve had countless conversations with women about their wardrobe struggles.

Time and time again, you’ve told me how much you want to declutter—but for some reason, you just can’t let go.

If this sounds familiar, don’t feel bad! I’ve been there too and the truth is it took me several years to go from deciding to declutter my closet to actually making any progress.

It took a lot of trial and error but eventually, I got there—and you can too!

To help you get started, I’ve put together a list of questions to help you declutter your closet. I hope these will inspire you to take a deeper look at your relationship with your clothes and also empower you to take action.

Title "7 Questions to Declutter Your Closet" in a bold font in a white box with a grey sweater and blue jeans in the background.

MINIMALIST WARDROBE TOUR

Before we get started—did you know that I’m a recovering shopaholic turned minimalist? At one stage, I turned my entire guest bedroom into a closet and I owned over a hundred pairs of shoes.

If you’re curious to see how things have changed, then check out this video for a behind the scenes tour of my current minimalist closet!

QUESTIONS TO DECLUTTER YOUR CLOSET

Now on to the main event—but first, a few words of advice.

As you read through this list, I highly recommend that you work through some of these questions in a journal.

I know this might feel strange but trust me, the biggest hurdle you’ll face while decluttering your closet is your mind.

You might not realise it yet but I can almost guarantee that there’s a lot of emotional baggage hidden in the back of your closet (along with those unworn cocktail dresses!).

Taking the time to do the groundwork first will make a huge difference because when you have the right mindset it’s so much easier to follow through with intentional action.

Let’s get started—here are seven questions to declutter your closet.

1. WOULD YOU BUY IT AGAIN?

Do you have anything in your closet that you “love” but you never wear?

If so, the problem might be that you don’t really love your item after all. Instead, you tell yourself that you love it because you don’t want to face the real truth: you made a mistake by buying it.

(This isn’t to say that you’re intentionally lying to yourself! But I’ve learned that often times, we tell ourselves creative stories to protect us from difficult feelings.)

A simple way to test this theory is to ask, “Would I buy this item again?” … and if the answer is “no”, then it’s time to let go.

2. ARE YOU WILLING TO TAKE CARE OF IT?

Every time I’ve decluttered my closet, I’ve come across a selection of clothing that I never wear—simply because I’m not willing to care for it properly.

For me, this includes anything:

  • dry clean only
  • that requires hand washing
  • that needs to be ironed
  • too delicate (out of fear I’ll damage it)

Everyone’s tolerance is different but personally, I know that if it requires too much maintenance, then I’m not going to wear it. (Or I’ll wear it once and then it will sit in my laundry basket for months!)

Ask yourself the same question—what is your tolerance for maintenance? If you know you’re not willing to care for something, then consider passing it on to someone who will.

3. WHAT WERE YOU THINKING ABOUT WHEN YOU BOUGHT IT?

As a former shopaholic, I’ve learned a LOT over the years about why we shop—and the truth is, it’s rarely for the reasons we think.

Usually, it’s not because we need something new. Instead, it’s often a reaction to fear or insecurity.

Maybe you’re feeling down because you don’t earn as much as a colleague or perhaps you’re feeling diminished because someone criticised a project you’re working on.

I’ve experienced both of these feelings and here’s how I responded:

  • I bought an expensive handbag because it’s what I imagined a wealthy woman would do.
  • I bought new stiletto heels because, in my mind, I associated high heels with power.

Of course, I wasn’t this self-aware at the time! 😂

It’s only in retrospect that I see how I used my clothing as a mask—to give myself a false confidence boost whenever I felt bad about myself.

Accepting this isn’t easy but until you acknowledge it, your item will always have power over you. I struggled to let go of those stilettos (even though I never wore them) because subconsciously, letting go meant letting go of my power.

One way to move forward is to reflect on what you were thinking when you made the purchase: did you buy it for yourself or were you more concerned with how others would perceive you wearing it?

4. HOW DOES IT FIT YOU?

OK, I know this one sounds obvious but you’d be surprised how often people want to avoid asking this question! When you’re decluttering your closet, one of the most important questions to ask is, “Does this fit?”

A few things to keep in mind:

First, remember that fit is not just about size. I can buy a pair of jeans in my size that technically “fit”—the waist and hip measurements are correct—but they might sag at the knees or be a little tight in the things.

These type of fit problems are often less to do with your weight and more to do with the garment design. Remember, we are all so different! If something doesn’t fit in the way you want it to, regardless of what it says on the tag, it’s OK to let go.

When your clothes are too big or too small … look, I’m a realist. I’m not rich so if I stopped fitting into my favourite jeans, I wouldn’t automatically toss them out! Instead, I’d keep them for a while because my body size tends to fluctuate a lot (I think this is true for most people). You’re not a “bad minimalist” if you decide to hang on to some things.

Having said that, make sure you’re not keeping things that are outdated, not really your style, or that you never wore in the first place—just because you’re nostalgic about the size!

Finally, remember that there is often a mental cost associated with keeping clothes that don’t fit. If there are dresses hanging in your closet that you can’t fit into, how does that make you feel?

If your unworn clothing makes you question your self-worth or inspires negative self-talk, then is it really worth keeping? Don’t be afraid to let go of anything that makes you think less of yourself (this goes everything—not just your wardrobe!).

5. WHEN CAN YOU WEAR IT?

This is another simple question that will help you declutter your closet. For anything that you’re not sure about keeping, write down the occasions when it would be appropriate to wear.

Here are some examples:

  • to the office
  • while running errands
  • Friday night drinks
  • to yoga class
  • while going for a walk
  • to a formal event

Then when you’re done, look at your list and compare it to your actual life.

For example, when I decluttered my closet I realised I had a lot of formal dresses and shoes—the kind of thing you’d wear out on a Friday night for drinks and dancing.

There’s nothing wrong with this … except that I’m the type that prefers my wine at home, on the sofa, while watching Netflix.

I loved my beautiful dresses and shoes but ultimately, I had bought for the lifestyle I thought I wanted (sometimes referred to as my “fantasy self”) instead of for the life I actually had.

6. DO YOU FEEL GUILTY ABOUT HOW MUCH YOU SPENT?

This is a really common problem—we keep things we don’t wear out of guilt because of all the money we’ve wasted.

I know this feeling too well because my shopping addiction definitely cost me tens of thousands over the years! And even now, if I think about it too much, I get an anxious pit in my stomach.

If you feel it too, then I know how tempting it is to give up on decluttering and to simply close your closet door instead. It’s not pleasant to face these feelings head-on.

But here’s the thing: years of experience have taught me that the longer you wait, the worse it gets. You are much better off confronting it and here is my top tip to help:

Think of the money as an investment in yourself—in your education and your wellbeing. You made mistakes in the past, now learn from them. Give yourself the gift of forgiveness and move on.

If you want more tips on how to deal with common decluttering challenges such as this one, then I invite you to download a copy of Mindful Decluttering using the form below.

Mindful Decluttering is a free guide and workbook where I share step-by-step exactly how I decluttered my home and life. You’ll also be subscribed to my weekly newsletter, where I share personal stories and advice about simple and intentional living.


7. HOW DO YOU FEEL WHEN YOU WEAR IT?

Here’s a final closet decluttering tip for you: try on your clothes and then ask yourself how you feel—both physically AND emotionally.

First of all, are you comfortable? Can you sit down, bend over, and reach for something on a tall shelf? If not, what is your tolerance for discomfort?

There’s no right or wrong answer. Some people are willing to sacrifice comfort for fashion and others aren’t—and it’s not my place to judge your choices. However, you need to be honest with yourself. (And personally, as I’ve gotten older, my tolerance for discomfort is practically zero! 😂)

Equally important, how do you feel emotionally in your clothes? I genuinely believe that what we choose to wear can have a huge impact on how we feel. (I know this isn’t the case for everyone and I wish I felt more detached from wardrobe—but regardless, I think it’s true for most people.)

For me, I know there are certain things in my closet I wear often because when I wear them, I feel like the best version of myself.

Aim to fill your closet with items like this and let go of anything that makes you feel uncomfortable in your own skin.

A STEP-BY-STEP GUIDE TO DECLUTTER YOUR CLOSET

Looking for more tips on how to declutter your closet? Check out this post for a detailed, step-by-step guide to decluttering your closet. I take a slightly different approach to what you may have heard before and this is some of the feedback I’ve received:

I’ve been sorting through my clothing hoard on and off for a year and must have read dozens of articles giving advice on how to do it successfully. I’ve made a bit of progress but still have too much stuff.

I tried Marie Kondo’s method but it left me feeling even more overwhelmed because I couldn’t distinguish between ‘joy’ and ‘donate’ items by this point!

On discovering your website, and in particular, the post on creating a simple wardrobe, I’ve had a lightbulb moment. I was in despair for so long and your writing has helped me to see things clearly again. Thank you!

I know that decluttering your closet can be challenging but I promise you that it’s worth making the effort.

There is something so empowering about taking ownership of your closet and in truth, it’s often the first step towards living a more intentional life.

If you found these questions and resources helpful, I’d love to hear about it! Alternatively, do you have any tips for decluttering your closet? Let me know in the comments! x

Author: Jennifer

Hello there! I'm Jennifer and welcome to Simply + Fiercely, a community of people striving to live simpler, more intentional lives. As a former shopaholic and workaholic, I know how it feels to live a life that doesn't feel true to what's in your heart. Fortunately, I've transformed my life and gone from feeling cluttered and confused to living a curated life filled with purpose and joy. Now I'm here to help you do the same. 👉🏻 Click here to get started!