How to Break Up with Your Clothes

Recently, I read Leo Babauta’s Simple Guide to a Minimalist Life. Mind blown. Afterward, I decided to participate in a minimalist project organized by Courtney Carver, where you wear a limited number of clothes for three months.

During the first month of the project, I wore a limited selection of clothing. To be precise, I wore 26 items of clothing. This number isn’t particularly important, and in fact it isn’t even all that precise (some things like underwear didn’t count), the point is simply that I consciously limited my wardrobe. If you’re really interested, you can see the full list of items I wore during October here.

As I expected, the world didn’t end when I wore fewer clothes. Nobody mentioned to me that I seemed rather sparsely dressed. In fact, nobody seemed to notice at all. Perhaps they were just kind enough not to mention anything, who knows. But I think the real reason nobody noticed is I was already wearing a fairly minimal set of clothing to begin with.

After that first month, I decided to clean out my closet. I had been avoiding this task, consciously or not, for months, if not years. I would sometimes stare into my closet once in a while and think, man, there are some things in here I never use. Yet it always seemed too daunting to tackle.

Why keep clothing you never use?

Here are some possible reasons:

  • You used to wear an item of clothing more frequently, but now use it rarely or never
  • You paid good money for a piece of clothing and are reluctant to get rid of it without having “gotten your money’s worth”
  • You might need the item sometime in the future
  • You are keeping something around as a spare in the event your go-to clothing is dirty
  • You think you’d wear a piece of clothing more often, if only you had something to go with it

Now you might be thinking, oh, what a great logical list of reasons! I want to clean out my closet too, I’ll just keep all that in mind and go through everything!


That won’t work, because what’s really going on is you are totally having a hard time breaking up with your clothes. Admit it.

Let’s look at this a litte more closely.

The Old Flame

Listen, if you are keeping a bunch of clothes that you never wear, you are holding them hostage. You need to get over them and set them free. Be strong, man, you can do this!

Granted, these clothes may have been a good match for you in the past. They might have been right for you, at an earlier point in your life, back when you wore cutoff jeans and terrycloth headbands. But people change, they grow. You, my friend, have grown.

If you’re keeping a perfectly nice shirt in your closet that you used to wear out to bars, but you never go out to bars anymore, then you’re just hoarding that poor shirt. Keeping it locked away when it could be enjoying itself, out at bars, on the back of someone else.

Why are you having such trouble setting it free? Would you miss the good times you had together? Are you afraid if someone else has your awesome going-out shirt, that you will be jealous?

Don’t worry, your shirt will still cherish your memories together. And you will cherish the memories with your shirt. But the classy thing to do is let the shirt go out and enjoy life. Don’t keep it cooped up in your closet.

The Bad Date

Perhaps you are reluctant to give away your piece of clothing because you bought it, thinking it was going to be great, but it didn’t turn out that way.

It’s OK man.

Sometimes these things happen. We make bad decisions. Don’t keep revisiting that bad experience every time you open your closet and see the collared shirt that is obviously too small and always was. Give the too-small-collared-shirt to someone who is smaller. Acknowledge that you should have bought it a size bigger, and that you have regrets.

Then let it go.

The One You “Should” Love

I know, it would be awesome if one day, it was raining, and you were going somewhere fancy, and you were able to bust out that awesome fancy raincoat that’s been sitting in your closet for 10 years, waiting for just such an occasion. Yet for some reason, this situation never arises, or maybe it does arise but you always end up wearing something other than the fancy raincoat.

Maybe you are just not the fancy raincoat type, eh?

So, why are you hanging onto the fancy raincoat? Did someone tell you you would look good in a fancy raincoat? Do you wish you looked good in a fancy raincoat, Clooney?

Listen, whatever the reason, it’s not fair to the fancy raincoat. You’re just leading it on. Tell it the truth, you just aren’t that into it.

Give it away.

The Fallback

Why are you keeping the suit pants that are kind of frayed, you might even say ripped, in the crotch? I know, probably nobody would ever notice the rip. And maybe, just maybe, your other suits might all be unavailable for some reason, and you might need to break out the busted one, and you’ll be glad you were saving it all this time.

No, no no. You are just leading the ripped-suit-pants on. You do not want to be with them. They are not right for you. Don’t keep them around, getting their hopes up.

Let them go.

Onto the Breakup

OK…perhaps now you’ve had some time to think about it, maybe there were a few tears, but you’ve decided to eliminate a few of those clothes that you’re no longer in love with.

How should you break up with them?

That depends on your personal style. Some people want to have an emotional breakup. Others want a “let’s just be friends” parting of ways. You may fit into one of these categories, or have a different style. It doesn’t matter, you just need to decide on your style.

Here’s one approach. Take each item of clothing you want to break up with out of your closet. Look it in the eye, or something. Thank it for being being a good shirt / raincoat / pair of ripped-ass pants. Tell it you had a good time together, but you need to move on with your life. Then fold it up and place it gently in a pile.

Do the same with any other clothes you want to break up with. After you’re done going through your closet, if you aren’t too distraught, too teary-eyed, start going through your drawers. If you need to take some time before you tackle the drawers, by all means do. This can be tough. You may want a few Kleenex handy, or your dog nearby, for unconditional love.

Now, take the pile, and put it someplace where you won’t be tempted to go back to the well. Give the clothes away, to someplace like Goodwill. Or if you’re feeling unsentimental at this point, just sell everything on eBay.

By the way — don’t donate ripped clothes, just throw them away, or recycle them if you can do that in your area. If you need to, right before putting them in the trash, light a scented candle and conduct a little goodbye ceremony. Then say goodbye.

New Loves

What is the point of breaking up with your old clothes? It frees up some closet space for one thing. But it also allows you to appreciate the true clothing loves of your life. The items you’re already wearing, but aren’t fully committed to, because you spend so much time thinking about the clothes you just aren’t passionate about.

Allow yourself to fall more deeply in love with the clothes you already love. You know the ones. They are the most comfortable clothes you own. The only reason you don’t wear them is because you feel an obligation to take your lesser clothes out on a date once in a while. But now, you have the space to truly enjoy your favorites.

7 comments… add one


  • […] attachment to all the marginal items in your closet. You’ll develop the confidence to break up with your old clothes. After all, it’s easier when you’ve had some time apart. Oh yeah, and you’ll be […]
  • Glad to see this from a male's point of view. I was writing a similar post and stumbled across your article. Looks like we were thinking about the same thing. I like the way your presented it. Well written.
  • [...] attachment to all the marginal items in your closet. You’ll develop the confidence to break up with your old clothes. After all, it’s easier when you’ve had some time apart. Oh yeah, and you’ll be [...]
  • [...] the number of clothes I wore, in an attempt to learn which clothes I actually loved, and which clothes I needed to break up with. This part of the experiment was a success: I’ve simplified my wardrobe and cleaned out my [...]

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