How to Finally Let Go of Clothes You Don’t Need

How to Finally Let Go of Clothes You Don't Need - The Well Dressed Life

Is it hard for you to let go of all those clothes hanging in your closet that you know don’t serve you well? 

The ones that are old and dated. 

The ones that don’t make you feel your best.

The ones that are “just ok” so you make due with them.


Then you are far from alone. 

Our Spring Wardrobe Challenge starts tomorrow!  So today’s post is designed to help you get in the mindset to be ready to let go without getting overwhelmed.

Purging Your Clothes is Emotional

I spent over ten years as a personal stylist, working with clients, helping them shop and create a wardrobe. Our first step together was always cleaning out and editing down their wardrobes.

It was my least favorite part of my job, but the most necessary. Almost every time I came home from that first appointment I was exhausted.  

Why was I so fatigued?

I realize after a few years; it wasn’t the physical task that drained me so much but the constant negotiations back and forth between the client and me.

Most clients, at least in our first meeting, wanted to tell me the life story of every item they ever purchased and debate every single piece we were purging.

The challenge became the longer I was in business, the faster I worked. I instantly knew what should stay and what should go.

Because I wasn’t emotionally attached to the clothes I could edit a decent sized wardrobe in under an hour. 

But it turns out I wasn’t the only one drained; clients would let me know they too were surprised how wiped out they felt after our time together.

Because our clothes are an extension of who we are, a link to our past and future, and almost entirely tied to our self-esteem parting with even the most unwearable piece can be stressful.

To make the experience easier for both of us, I had to figure out a way to not only streamline the process but also lessen the rush of anxiety many clients felt.

Since I’ve stopped working with clients, we’ve published countless posts on how to edit and organize your wardrobe (here and here).  We even created our seasonal 4 Week Wardrobe Challenge (starting tomorrow here on the blog and over in our private Facebook group). 

But we’ve never explicitly talked about the mindset you need to move through the process.

With Spring in the air, it’s the perfect time of year to talk about editing and paring down our wardrobes. If you have a grasp of the steps but struggle with actually letting go, there are a few things you can do to lessen the strain and stress.

How to Purge Clothes

Know Your Style

You cannot curate your wardrobe if you don’t know your style.  This is an absolute MUST. If you don’t know your style, you will not be able to create a framework for what to put in and take out of your closet.  Before you attempt to edit your wardrobe, take some time to figure out what you like.

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When we worked with clients, before we even entered their closet, we asked them to pull pictures from magazines and catalogs or create a Pinterest board of looks they loved.  

Giving yourself a visual will help you see a common theme. Do you like pants more than skirts? Solid colors or bold prints? We’ll deep dive into this more tomorrow with an incredibly effective exercise that readers over the years have loved.

Going through these steps prior to starting your edit made a huge difference for our clients.  It gave them “permission” to let go and provided some much needed clarity and focus. 

When you are struggling to retire an item, hold it up to your inspiration pictures and ask yourself, “Does this get me to my desired personal style?”

If the answer is yes, you keep it. No, let it go. 

You Already Spent the Money

“How can I get rid of something I spent money on and barely wore?”

We all know how frustrating it feels to you look at your donation pile and see nothing but wasted money. We’ve all been there. 

But once you can grasp the idea of a “sunk cost,” that you already spent the money, whether it’s hanging in your closet or someones else’s, at this point, doesn’t matter. It will be so much easier to look at it as clutter and remove it. 

Hanging on to it, and not wearing it, doesn’t give your purchase any value. Often, it does the opposite and becomes a negative, or a pain point in your closet. You look at it and become frustrated and annoyed. 

Is it in excellent condition but doesn’t work for you? Sell it on Thredup or Poshmark (see our tips here). If it’s in decent condition but not sellable, donate to someone who can benefit from it and move on.

It’s Not Coming Back in Style.

I often say I care less about making you look stylish and more about making you look current and modern. Looking dated, especially as we age, is what we’re trying to avoid.

While trends come and go, each new iteration has nuanced details that make it modern.  Unless we’re talking about a Chanel tweed jacket or YSL suit, I promise you, 90% of what you own is coming back.

So how do you know when something is dated?

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Well, the inspiration picture exercise above helps.  Do you see what you have hanging in your closet in your pictures? Don’t look so much at the style, rather, look at details like buttons, pocket placements, length and widths of pants, where the shoulder sits, color saturation. 

Think of it like this: the classic pair of black pants you bought in 2000 is now TWENTY years old. The styling, the line the construction and fit – are all outdated. 

Consider asking your closest friends or even your kids for guidance. As the mother of soon to be teenagers, my girls are frighteningly good at giving – ahem, brutal, fashion advice.

The point is, you might need a fresh set of eyes to see what you’re wearing objectively.

* And I know that everyone has that one piece that works with everything and lasts forever, but that is a unicorn. The blazer you bought at Kohl’s on the clearance rack is not that piece. 

Don’t “Save” Your Stuff for Someone Else 

One of the most surprisingly consistent things clients would say when we were cleaning out their closets, and I held up a piece to remove was, “oh, not that, I’ll see if my daughter wants it.”

I eventually realized they were using that as an excuse not to have to make a decision.

“No she doesn’t! She’s 12!” 

So, let me say this with love, with few exceptions, your friends and neighbors don’t want what you are giving away. Don’t pass your old stuff on to other people; you’re just giving them more clutter.

The exception is, of course, heirloom quality, a timeless designer or sentimental pieces.  I have several pieces put aside for my daughters.  

If you are no longer wearing them, have these items cleaned and stored properly, so they stay in good condition. I have a few vintage bags put aside for my girls, the white suit I wore at my rehearsal dinner, and some designer pieces I splurged on that don’t fit anymore.

Other than that, don’t use “passing” down a piece as an excuse to not have to make a decision about it. 

How to Finally Let Go of Clothes You Don't Need

Take It Out of Your Main Closet

If you have items you are on the fence about, don’t stress.  Move them to a separate closet or store them in a box.  After a few weeks, or even at the end of the season, if you haven’t reached for them, you know you can finally let them go.

Same for clothes you’re hoping to fit into again.  If you’re on a weight loss journey, don’t keep those pieces in your closet. I hate the idea of waking up and having to sort through garments that are too small.  Move them into a different closet, or keep them in a bin under your bed. 

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When you’re ready to try them on again, use the same exercise and principles you used for the rest of your closet.  

Fit Doesn’t Mean You Keep

Remember, just because something fits doesn’t mean it’s for you. As women, we are so used to the struggle of finding things that fit; we often ignore whether we like it or not.

I found this out personally when, after I had my last baby, I resubscribed to Stitch Fix for some postpartum clothes. I was so happy something zipped up I often kept the piece with no thought to whether I liked it.  I eventually ended up spending more money than I wanted that turned into a large donation pile. 

Think about how many things you have that you are lukewarm about in terms of style, but kept because you’re just happy it fits? (Women around the world raise their hands.)

Your Closet is NOT a Department Store

You don’t need to stock your closet like a department store. While I’m far from a minimalist, the sheer volume I’ve seen in closets is incredible.

The biggest issue was women buying things because they were on sale. Not because they needed them, liked them, or had any interest in wearing them. They simply purchased the garment because it was at a discount.

Not only does that fill your space with unnecessary “stuff,” it’s a gross waste of money.

Making a habit of thoughtful, considered purchases will help keep your closet organized, it better for your wallet, and helps limit the waste we so frequently in the retail industry. 

The Spring 2020 Wardrobe Challenge 


Getting organized and building a wardrobe you love is a lot like getting fit and healthy.

There is no quick fix or magic wand to turn it around quickly. It takes a great deal of time and discipline. Editing your wardrobe is like those first few workouts back at the gym. It’s miserable, but then you feel great, and then it gets easier.

Tomorrow starts our four-week Wardrobe Challenge: a series I designed based on the 3 step system I used to work with private clients.

Every Friday, here on The Well Dressed Life, I’ll post a series of activities created to help you:

(1) figure out your personal style

(2) ruthlessly edit your wardrobe

(3) figure out what you need to create a wardrobe you love.

It’s totally free, just fun and helpful resource for our readership. For extra support, lots of useful conversations and support can be found in our Private Facebook Group. If you request entrance, please be sure to answer all three questions at the prompt, that’s how I approve membership.


How to Finally Let Go of Clothes You Don\'t Need

10 thoughts on “How to Finally Let Go of Clothes You Don’t Need”

  1. I always knew my style, but then I turned 50 and realized stores don’t have much for customers like me. Then, I started to hate shopping, stopped knowing my way around the stores, and now I feel overwhelmed. Not only do I not know what suits me, what I love — but even if I did I wouldn’t know where to buy it. Based on the catalogs that come to my house, I suppose I should load up on Eileen Fisher? Help me!!

    • Kristin,
      I had to smile at your comment about clothes for the “over 50” woman. I especially had to laugh at the Eileen Fisher comment. I know exactly what you mean. Now having just turned 60, I also feel the same way as you with the change in personal style and not finding what we really want or need. Maybe we can get Megan to do a post on wardrobes for the older woman. 🙂

  2. These are great tips. I struggled so much with this, especially when I still had tags on stuff. But once it was out of my closet I felt so much better, less guilt, and then ended up with just stuff I love. And, then you can also see the holes better and can add accordingly.

    My problem still lingers with shoes, but I’m getting better.

  3. Great timing for this post Megan! I decided that I would finally get rid of a skirt that I literally moved back and forth between summer storage and winter storage for (gulp) 10 years without wearing it once. Oh the energy wasted that I could have used on shopping:)

  4. This has been great. I have been the worst at cleaning out my closet. At one time when cleaning out my closet, I decided to give some outfits a second chance. My mindset at the time was: if you don’t wear it next year, it has to go. Well some things never went. Then when I would finally reached the stage of actually removing it from my closet, I moved everything to a space room we had and would keep the discarded clothes there just in case. After all, what if I needed it? What if it came back in style. Through your suggestions and subtle push, I have taken the big leap and really cleaned out my closet and the spare room. I almost cried as I drove my clothes to the local thrift store. The gentleman who grabbed the bags from me tossed them onto a large conveyer belt and I actually cringed. But I feel free and I actually that I have a clean palette to work with. I have slipped back, but I am making progress. And yes it is an emotional rollercoaster.

    • This is called an “evergreen” post, one that is regularly updated with relevant, timely content. Today’s post as been edited with new information, more tips, greater detail and updated images.

  5. Thank you, I needed this post! I’m so emotionally attached to my clothes. I will need to re-read to really apply the needed ruthlessness to pare down my bursting (but also small) closet.
    When we went through a financially difficult time several years ago, I was the blessed recipient of hand me downs from 3 different women in our community. Their clothes were beautiful, and brands that I could never afford on a good day. It felt foolish and ungrateful to pass any of it on, so I ended up with way more than I needed. I still struggle with guilt getting rid of those pieces – even though it’s been 5 years in the “clear” financially.
    I also have favorites that I love so much and wear all the time – some I’ve had for close to 10-15 years! They haven’t worn out yet, and I have a hard time “seeing” if they’re out dated. It’s hard to justify buying similar updated pieces when I’m stretching my clothing budget to fill in other holes. Sigh… why are clothes so complicsted???
    I DO have to say though, this blog has been IMMENSELY helpful in helping me see what I like and why, and what works/doesn’t work and why. I don’t feel so panicky anymore, and have SO much more confidence making any wardrobe decision! Thank you Megan!!!

  6. I absolutely love this post! I am guilty of all of these: hoping for a body I’ll never get back, feeling guilty for money spent on clothes I don’t wear, too much in my closet, emotionally attached, and not being able to see the modernity. Thank you for this! I am saving this post because I will need it over and over, I’m sure!

  7. Not sure where my husband fits into this algorithm but he has clothes crammed into his half of our closet that haven’t seen daylight in 15+ years. He won’t even discuss going through them for donations. I did manage to pry about 20 ragged, stained tee shirts out of his hands. Victory was mine!


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