I have noticed in cleaning out my own closet (and helping others clean theirs) that we tend to use the same phrases over and over again. These phrases initially seem like a reason to keep an item, but are actually red flags that it is time for these items to go. I’m hoping that addressing a few of them here, with some stories of my personal struggle, will keep you from falling for the same mental traps that I do.
- “I really should wear this more” // usually this phrase comes out when we have dragged some item out of the depths of a pile. It is something we have not seen in a long time, but we remember liking it?

Every time I pulled this heart sweater out to wear it, I thought “I really should wear it more” but then I would wear it and remember why. It is just not very comfortable, fits a bit tight for my taste, and the sleeves always left painful imprints on my elbows. Yes, it was cute, but I will never reach for it over my other more comfortable sweaters. So this most recent cleanout, this sweater was gone.
What you should do: when you have uttered this phrase, that doesn’t mean an immediate no, but you should take a minute and think long and hard about the item. Why don’t you wear it more? Why was it in the bottom of this pile? Often the reason we don’t reach for items we can clearly see is the same reason we don’t search for items that are long forgotten. Either they don’t fit, or they aren’t our style anymore, and just in general they aren’t serving us. If you get to the end of this thought process and still decide to keep the item, then make sure it is in a prominent place. If you haven’t “worn it more” by the time your next closet clean out rolls around, then get rid of it.
- “It was a gift!” // usually happens when you come across a thing that you do not actually enjoy wearing, but a person that you care about gave it to you so you feel guilty for getting rid of it.

This red dress was a matching set of dresses my grandmother picked out for celebrating the 4th of July one year. I liked it in theory – I am generally into oversize printed dresses as layering pieces and the ruffle at the bottom could look cute under a sweater. However, the few times I did try to wear it again I just didn’t like it. So in the next round of cleanouts, this dress found itself in the going pile.
What you should do: when this comes up, ask yourself why you are really keeping this item. Is it serving you or is it taking up valuable storage space, and cluttering the things you enjoy wearing? Will the person remember that they gave it to you and ask about it? If you aren’t going to wear it, and it is likely that the person will not remember giving it to you, then you should get rid of it. If you just cannot bring yourself to get rid of the item, try finding a storage solution that doesn’t keep it out in the open.
- “I used to wear this all the time!” // usually occurs when we see an item that we used to love, but have since stopped wearing for whatever reason. We eagerly try it on, and often quickly discern why we stopped loving it.

This purple shirt with fun sleeves was a hard one to get rid of. In fact, for me the “used to love it” line is the most dangerous. It is hard for me to admit that a thing just does not work for me anymore. This shirt was so fun, a great color, and gave me all the French provincial vibes I adore but when I tried it on recently it was just. too. tight. It was uncomfortable to wear, and required layering underneath since it’s so thin. I knew that I wouldn’t wear it anymore so it was time to go.
What you should do: this phrase is an acknowledgment that you used to love it, but clearly don’t wear it anymore. Whatever the reason – if you don’t reach for it over other items in your closet then you don’t need to keep it. Unless it is something unique, timeless, or valuable, I would say “used to love” items are ready to go. If they are still in good condition then someone else will love them just as much. If they are falling apart beyond simple repairs, then they have served their time.
- “Oh this would be so cute if…” // usually shows up when we find an item that we’ve been meaning to edit for a long time. A shirt we’ve been meaning to crop; a skirt we wanted to hem; some pants that we wanted to adjust the waistline on.

Ah this skirt. I bought it on a last chance sale (i.e. non-returnable) thinking that it was only a few inches too big and I could easily fix it. When the skirt arrived, I realized a few inches was more like 5 inches where I wanted it to sit. After my first mend, I still wasn’t happy with it and I knew I wouldn’t want to put the effort in to mend it again. Someone else will be happy to have a skirt that fits them, and I don’t need to be giving space to an unfinished project.
What you should do: with these items I give it the “right now” rule – am I willing to sit down and fix this right now? If I am already doing a closet clean out, then I know that I have the energy and motivation to complete the task, and often simple edits I can whip out in that moment. If I am not willing or able to do it right now, then it is time for it to go. If right now doesn’t work for you, give yourself a time limit that does. Maybe until the end of the week works better for you. A time limit is the key – these items need an expiration date. Unless you’re a seamstress regularly sewing and mending items, the likelihood that this will continue to be an unfinished project taking up space is high. Make peace with the loss and move on.
I also want to say about this line — if the modification is to your body and not to the garment then gone it should be. “This would be so cute if I was more tan” or “… if I was thinner/thicker” means that the piece was not made for you, is not serving you, and needs to go. Clothes should fit you, not the other way around, and all bodies are beautiful and valid as they are ๐
- “I spent so much money on this…” // usually comes up with an item that we regret buying. Either it was an impulse buy, a trendy piece that didn’t work out, or a vintage/thrifted item that was ‘such a good deal’ in the store but not actually right for you.

THIS. DRESS. AAHHHHH… So I don’t even have any pictures of just the dress. I originally purchased it from someone who made it for me but the sizing was off. So I purchased it again, and sent them measurements, hoping that it would fit better. The new one did fit better, but I realized the the style was not working for me. I spent so much money on these two basically identical dresses that just didn’t work out. Time to cut my losses and let them go to others who will like them more.
What you should do: like the items above, you might just have to make peace with the loss and move on. There is a reason you don’t wear these items enough to justify the cost; the guilt is a red-flag in and of itself that this item is not serving you. The goal of a closet clean out is to have readily available the pieces we love to wear, and that make us feel good. Items that bring up guilt don’t accomplish that goal. Perhaps you can list it online and recoup a bit of the cost? Or take heart in the fact that while you don’t love it, someone else certainly will.
- “Oh, this actually fits!” or “Well, it fits.” // usually happens when we try on an item we initially wanted to get rid of; the surprise is because we don’t actually wear it that often.

I owned this sweater for a long time because it fit me really well and I liked it in concept. However, I never wore it for various reasons – it was hard to style, it was a bit small for me – but honestly I just did not like it as much as I thought. It was not my style. So while it passed many cleanouts because it did fit me well, I finally gave it up. Someone else will love this sweater and wear it all the time, no need to it to be taking space in my closet.
What you should do: This is a trick of the mind – we think because it fits that means we should keep it but fit isn’t the only reason that an item deserves a spot in your closet. Maybe it isn’t really your style anymore or doesn’t fit your current climate or lifestyle. Like the things we used to love, these items end up cluttering the visual space in our closet and hiding the things we really love to wear. There is a reason you didn’t know that it fit – and it’s probably time for this item to go.
Often we know as soon as we see an article of clothing whether it should stay or it should go. I am hoping that recognizing some of the phrases in you hone in on your instincts and curate a closet that makes you excited to put on your clothes in the morning. After all, clothes should make us feel happy and confident – not guilty or uncomfortable.
What are some common pitfalls in your closet clean outs? Do you recognize any of the above phrases? Did I miss any the should be addressed? Let me know in the comments below.