Why Hanging on to Skinny Clothes Hurts You - and How to Get Free

We hang on to clothes that clutter our closets for all the wrong reasons.  

I'm in my early 60's.  As far as clothing sizes go, I've worn everything from a size 5 (briefly) to a 3XL.  I can relate to someone's desire to hold on to their skinny clothes until they fit again.  After all, you spent good money for them.  They remind you of your younger days, and they're still in good condition.  Yes, I know all the excuses.

Home organizer Bonnie Borromeo Tomlinson is blunt about it:

Hands down, the number-one reason most clients hold onto clothes that they no longer wear is the agonizingly inaccurate "incentive" mentality – the holding onto of clothes, one-to-several sizes too small, as inspiration to get thin.  It's a popular tool, and one that rarely if ever actually works.  Of all the motivational measures you may find to lose weight, this isn't it.

vintage skinny jeans

The awful truth

In the meantime, that old pair of jeans is working against you.  Consider the self-torture you endure every day:

  • Those clothes are a constant reminder of who you were, rather than who you are today.
  • Those clothes are a constant reminder of the money you spent – just one more thing to feel guilty about.
  • Those clothes aren't in style.  Even if you lose the weight, you might not want to wear them again.
  • Those clothes were purchased for a younger person.  Even if you lose the weight, they might not suit your current stage of life.
  • Those clothes hold you back.  If you lose the weight, you'll want to celebrate and treat yourself to new clothes.
  • Those clothes take up room you could be using for clothes you can actually wear.  Your jam-packed closet is mostly useless.

And finally, those clothes can never motivate you to lose weight because they make you feel hopeless and stuck.  As you try on piece after piece, looking for something you can wear, and see yourself in things that are too tight, that emphasize your less-than-perfect areas, that sag and gap and inch up, your confidence plummets, and your insecurity and depression grow.

Bottom line: incentive clothes do not work!

Get yourself free.

young women in cocktail dresses
So pull it all out.  Everything!  From every closet, drawer, and shelf.  Shoes, coats, pajamas, and dressy clothes.  Do the laundry so you don't miss anything.  You want a pile containing every piece of clothing you own except what you're currently wearing.

Sort the mess into two piles – what fits and what doesn't.  Now is not the time for excuses or pretending.  Now's the time for complete honesty.  Can you get into it, or can't you?  And if you can get it on, does it look the way you want it to?

That sexy cocktail dress you wore to your cousin's wedding and never again – maybe you can just about fit into it, but do you really want to show that much skin anymore?  That top that used to be so cute on you – does it really complement your older hair and skin and that slight softness around your middle?  Those pants that were never quite right to begin with, but you got for such a fantastic price – has time helped them to improve?

I'm going to be honest with you.  This won't be fun.  You're going to feel pretty awful.  The money you spent, the wasted closet space, the regret that you didn't choose a lifestyle that would keep you thin(ner) and fit(ter), the fact (the undeniable fact) that you have aged.  This could become a deep, dark pit that you keep falling into.  It might seem easier to shove it all back where it came from and just live with closet chaos.

I know some of you are in there with me right now.  You know exactly what I'm talking about.  Get teary if you need to.  Get some caffeine or maybe a small piece of dark chocolate.  Take a few deep breaths.  You are worth this.

Now pile all that stuff that doesn't fit and get it out of the room.  (Yes, you can sort through it later and see if there's anything worth donating to Dress for Success, the Goodwill, your local theater group, or the animal shelter – they always need rags.)  For now, you don't even want to see it any more.  Stop torturing yourself.  That's over and done.

Now you're left with clothes that fit.  But some may still be wrong for you.  Maybe they're stained, stretched out, faded, pilling, or just plain ugly.  If you've struggled with your weight, like I do, you may wear clothes that cover you adequately but don't make you feel in any way attractive.  Maybe you've thought, "What right do I have to feel good about myself?  I don't deserve that."

You've seen Queen Latifah, right?  Melissa McCarthy?  Mo'Nique?  Adele?  How about GĂ©rard Depardieu or Jack Black?  Do they have the right to feel good about themselves?  It doesn't matter that they're not thin – they're talented and intelligent.  They have a lot to offer.  So do you.

So, some of what actually fits needs to be added to the "out pile" as well.  Go on – get it out now.

Now what?

confident woman
Rehang what's left.  There may not be much, but no matter what, every time you open your closet to get dressed you won't have to hunt through a crowd of useless things that make you feel awful.  You're going to put on clothes that fit well, look good on you, and make you feel good.

You may find that your posture improves.  You breathe easier.  Maybe you even smile more.

Why would that be?  You haven't lost weight or bought anything new.  All you've done is free yourself from feelings of failure and self-recrimination.

(Oh... that's all, huh?)

In a few days, sort through the "out pile," and quickly decide what's worth donating, selling, or even gifting to your sister or a friend.  Some things will need to be turned into rags or thrown away.  

Will you have any regrets?  Maybe.  Regrets that you hung on to stuff for so long and made yourself and your closet miserable.  Meanwhile, you have a minimal closet that forms the basis for a useful and beautiful capsule wardrobe.

9 steps to a wardrobe that works

For those of you who like a step-by-step, here's the summary.

1.  Do it all at once.

Don't attempt this unless you have a couple of free hours.  Otherwise, you're going to make a huge mess and wind up having to sleep on it.

2.  Investigate the hiding places.

You know – the back room coat closet, and that gym bag you don't use very often that's tucked under the stairs.  Slippers shoved under the bed and covered with dust, and the pink faux fur jacket your daughter used as part of her Halloween costume last year.  Everything out.

3.  Do the laundry.

You want to include everything in this big clear out.

4.  Ask just one question.

You're only going to make two piles, and there's only one question to ask.  Not "Could it fit if I did ______?"  The question is "Does it fit?"

5.  Get the "out pile" out.

Don't worry about what you're going to do with it yet.  Just remove it.

6.  Revisit the "it fits" pile.

Now you get to ask a few more questions:

  • Is the piece still in good shape?
  • Does it fit well?
  • Is it attractive on?  
  • What makes it attractive?  (Color, cut, fabric, neckline, sleeve length, etc.)
  • Do I still like it?
  • Do I have actual use for it? 

If the answer to any of these questions is no, add the piece to the "out pile."  Only the 100% yes pieces can stay.

confident woman
7.  Live with it for a week or two.

Wear what fits in rotation, and notice if there's something you consistently pass over.  That orange blouse you never choose?  Chances are it's just closet filler.  Add it to the "out pile."

I know you're saying "If I get rid of everything I'll have nothing to wear!"  The truth is, you already had nothing to wear.  What's left is all you have worth wearing anyway.

8.  Deal with the "out pile."

There are several ways you can go here.  But remind yourself that nothing is coming back into your closet or dresser drawers.  You're going to zero out this pile.

Most of it can have a new life:

  • Invite your sister and your friends over and let them take what they want.
  • Have a yard sale, and save the money for a wardrobe shopping trip.
  • Sell them through a consignment shop (local or online).
  • Take winter wear to a homeless shelter.
  • Donate to the Goodwill or another favorite charity.
  • Downgrade old tee shirts to cleaning rags (your local animal shelter may take some).
  • Toss what's left (hopefully it won't be much).

9.  Shop mindfully.

Don't just rush to the store, even though your new, more customized wardrobe may be small.  Think about what you're missing, what you really need, and then go find it.  Do not bring home any "This might work," "This is probably good enough," or "It's not quite right but it's on sale" pieces.  If you can't find the fit, quality, style, or color you're looking for, keep looking.

One more thing

Now maybe you've read this post and thought, "This doesn't apply to me.  I'm the same size I was in high school."  Well, good for you.  Are you the same person you were in high school, 15, 20, or more years ago?  I don't think so.

Borromeo Tomlinson asks,

Do you have several lifetimes sharing space in your closet?  Do you have an abundance of impulse purchases?...  Or do you just have too much because it's "still good"?

This system works the same for any overcrowded wardrobe.  If fit is not your issue, but your closet is over-stuffed, then something else is causing the problem.

Bottom line, these are just clothes.  They came off a store rack with thousands of other identical pieces.  They're replaceable.

What's not replaceable is your self-respect when you feel ugly and defeated.  The time you spend digging and searching and trying to get dressed.  The space you're giving to things that do you no good.  The money you've lost on purchases that weren't right for you.

I want to feel free, confident, and worthy.  That's how I want you to feel, too.  And by the way, if you want incentive to lose weight or get fit or anything else, those feelings are going to be far more effective than any pair of old jeans.

Are you ready for the newest edition of my best-selling book, The Minimalist Wardrobe: Buy Less, Choose Well, and Feel Confident Every Day?*  With 7 additional chapters, and over 40 pages of new content, this 3rd edition is sure to inspire you to create a wardrobe that passes the "feel good test" and lets you wear your favorite things every day.

* This blog is reader-supported. If you buy through my links, I may earn a small commission.


  1. Great article, Karen. I have mostly conquered my clothes closet but I still make impulse purchases or buy things that just aren't right for me. Thank you for the encouragement to be patient and purchase clothes that will help be build a wardrobe that looks and feels good on me.

  2. Karen, I think you wrote this for me! You must have sensed the closet in my house where I have “incentive” clothes waiting for me to lose 50+ pounds. And, you’re right - looking in that closet is depressing. Time for some closet cleaning!

    1. Good luck! Now you can find other, positive ways to inspire yourself.


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