Cleaning Out Your Closet: Common Pitfall Phrases

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 🙂

  • “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.

How To: Shop at Thrift Stores

As tempted as I am to start this post with a quote from Macklemore’s song “Thrift Shop,” I won’t. I will, however, explain that the feeling of the song (and the reason it quickly became popular) is exactly why so many people love shopping at thrift stores. The thrill of the hunt, and the quest for a bargain can be intoxicating. It can also be why so many find it difficult and laborious.

One time, while flipping through the clothes in a local thrift store, my mom stopped and looked at me.

“I will never understand how some people look like they shop at the thrift store. I shop at the thrift store but I don’t look like I do.”

It took me a minute but I realized exactly who she means – the people who pick out the ill fitting denim shorts that look like they are from the eighties and pair them with a t-shirt for a resort they’ve certainly never been to. The people wearing the button down denim coverall dress that goes to their ankles without a hint of irony. It is a look that I think most people dread (though if it’s your thing – rock it!) and I believe is another common reason for hesitation to really enjoy thrift shopping.

Yet thrift shopping can be a beautiful thing for both your closet and your wallet. It’s no secret that thrift stores offer clothes at an extreme discount, since they are all donated. A thrift store can be a great place to upgrade your style if you’re on a tight budget, try out a trend without investing too much money, or fill out basics that you wear a often.

I’m hoping that these tips will help make thrift shopping into something that is easy and enjoyable for anyone willing to try.

thrifted items pictured: purple leather jacket, gold velvet shirt dress, blue velvet dress

—–> Tip One – Have a Broad Goal in Mind

Goals or quests or things you’re hunting (or whatever you call it) make thrift shopping fun and provide structure and purpose to a place that’s built around chaos. Many shoppers suffer from two common thrift goal problems. The first set has no goals at all, and often leaves the store regretting half the things they purchased. The second set has goals that are too specific and leave empty handed and frustrated. I like to have two or three main goals that I keep pretty broad: comfortable dress pants, black sneakers, and chenille sweaters have all been thrift shopping goals of mine in the past. Sometimes I find what I’m looking for, and sometimes I don’t, but making the goals broader gives more room for success. Having multiple goals helps too, because if you realize it’s just the wrong time or place for one item, you still have other things to look for and it won’t feel like such a waste of time. Keep an open mind though – if you’re too laser focused on your goals you might miss something amazing.

—–> Tip Two – Size Is Just A Number

Never has this statement been more true than when you’re at the thrift store. If you struggle with sizes, try starting a thrifting experience with self acceptance – this is who I am right now, and that’s okay – because starting positive will color the experience in a positive light. Also, remember that at the thrift store you’re working with sizing through the ages. A 10 in the seventies won’t be the same as a 10 today. Not to mention that sizing can change drastically from brand to brand. I start with a base range of medium for shirts and 10-14 for pants. If I try on a bunch of pants or shirts in a row that don’t fit, then I expand the range in whatever direction I need. Remember: no one will care what the number says if the clothes fit well.

thrifted items pictured: grey pants, red sweater, green pants

—–> Tip Three – TRY EVERYTHING ON

This is probably what I would call the golden rule of thrift shopping, so I will say it again – try everything on. I don’t care if it’s not your style, or your size, or you don’t think it will work, or whatever… you really do not know for thrifted items until you try them on. So many of the items you pick up and laugh about or scoff at will end up being favorites, and just as many pieces you think you love might not work. If it catches your eye then it’s worth trying on.

—–> Tip Four – The Buddy System

Thrift shopping generally works better if you bring a friend (or a few) for several reasons:

  • having someone to chat with makes sifting through the piles and piles of things less of a chore
  • a friend makes a good editor to help you if you are on the fence about an item. Sometimes even just saying your reasoning for or against an item out loud is enough and this comes off a lot less crazy if you’re with someone.
  • more sets of eyes means higher likelihood that you will find what you are looking for.

thrifted items pictured: teal sweater, purple skirt, flower raincoat

—–> Tip Five: “But It’s Only $3!”

This is by far the greatest thrift store struggle and one that leads to the most post-thrifting regret: buying an item because it is cheap. When an item of clothing is surprisingly cheap, a switch flips in our brain and we start to rationalize why it might be worth it. This is the reasoning behind the impulse shelving at stores – it’s easy to throw a bag of chips or candy bar in at the last minute because it’s only ___ amount of money. This is even more problematic when it comes to clothes, especially if there’s one thing we already like about an item. Here’s an example from my most recent thrift:

Sifting through the sweaters, I find a cardigan in a light peach color made of suede. The garment fit okay, and it was so soft, and it was only $3, and I was so tempted to buy it.

I eventually decided against it because a) I don’t really wear suede, b) it’s not a color that goes with anything else I own, and c) I knew I wouldn’t wear it

When you’re stuck in the impulse, it helps to ask yourself some key questions that weed out things that just won’t fit in your wardrobe. Here are some of the key questions I use:

  • Does this go with things I already own? try to mentally create three outfits
  • Do I actually like this color/style/fabric?
  • Is this an item I usually wear? i.e. if you’re always hot but tempted by a coat, you should probably put it back
  • If I was exhausted, would I pick this item to put on?
  • Where/when would I wear this item?

If the item misses three or more questions in a row, then it’s not worth it.

Any of these tips helped you? Feel like you’ve tried all these and are still stuck? Have any tips of your own? Have a specific question about thrifting? Feel free to comment below!