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Transform Your Closet with These Five Decluttering Questions

If decluttering your closet is on your list of intentions this year, this is the place to start. Throughout this year I want to talk about an unpopular opinion, shopping your own closet. My aim is to help people like yourself detox from the overwhelming messages of buying something new, and help you make more informed and intentional decisions around what to buy.


This is not me saying don't buy anything new for yourself. But I am saying before you do, ask yourself do you really need it? This exercise will help you get to the bare bones of your closet so that when you make that shopping list this year, you know exactly what you need and how you will style it. We will start with these 5 questions to help you decide if you need to toss, donate, or keep an item in your closet. I like to do this instead of tell you what you need because everyone's style is different! These questions should help drive your decision making while you purge your old closet and reveal your new closet for the new year.


What you will need for this exercise.

  • 3 bins or boxes. Labeled donate, keep, toss.

  • hangers

  • good music

  • food

  • drinks

  • friends are a bonus


These questions are very basic. They can get more in depth but for now I am keeping it simple. Once you gathered all your supplies, found a playlist, the pizza is hot and the wine is ready, you can jump in. I suggest touching all of your clothes during this exercise. If all your clothes are not present (they are in the laundry for example) repeat these questions when you get hold of them. Let's start!





  1. Did you wear it in 2023?


Honestly? Did you wear it? Not if you planned on wearing it, not if you were going to wear it for that thing and got sick and decided not to go. If you did not wear it at all last year, immediately put it in the donate pile. If it still has tags on it, see if you can return it and get money back or credit. We are leaving no coins on the table this year. If you didn't wear it at all last year, there is a strong possibility that you won't wear it this year.


2. Did you gain or lose weight recently?


If you did, I would highly suggest trying on any clothes you think you want to keep. The object of this is to only have items in your closet you absolutely love. If anything isn't fitting correctly, donate it. Your clothes are meant to keep you comfortable and help you feel good about yourself, therefore only you can determine if a fit, fits you. I personally have oversized clothes I love in my closet. They may not be "flattering" to others, but they are to me. I also have some pants that are still a little snug, if they do not fit better in about 6 months, I will choose to donate them.


Trying on your clothes at this stage prevents you from putting something on from your new closet that doesn't feel good. Are your jeans comfortable when you stand but really uncomfortable when you sit? Is a dress amazing but you notice you fidget a lot when you wear it? Is there a jacket you own and you can't lift your arms? Think about how you live in your clothes to determine if something "fits". Anything that doesn't align with your definition goes into the donation pile.


3. Do you like it?


I know this seems like a silly question, but depending on where we are in life or where we are coming from, there may be clothes in our closet we actually do not like. For example, I worked for a second-hand store for 3 years. I naturally accumulated a lot of clothes. When I decided to leave that environment and switch jobs, the clothes that were once functional for that job didn't translate to the other. I kept some but gave away a lot.


If you are wanting to explore other styles this year, there may be items in your old closet that will not fit your new closet. It is ok to change and grow! If you like the item, have worn it in the last year, and it feels good when you put it on, that's a keeper! If you are standing in front of the mirror tilting your head from side to side, that may not be the piece to move forward with.


4. Is it damaged?


Things happen. I have a wool coat I thrifted, and the lining is demolished. Since it is the lining, I plan to get that repaired. If you are willing to spend the money to get the items that are damaged repaired, make a pile to take them to the tailor. If you know you are not that disciplined, toss it. Nothing is worse than trying to get dressed and you forget a shirt has a hole or pants have a bleach stain.


5. Is it a one hit wonder?


The making of your new closet is rooted in being able to pull multiple outfits from it. It is the gift that keeps on giving. Depending on how you feel about repeating clothes, there may be items in your closet that you bought for a very specific reason and never wear again. That Hawaiian themed birthday party and you bought a tropical shirt? That wedding you were a bridesmaid and somehow the dress is still in your closet. These items may have served a purpose, but they are taking up more space in your closet than on your body. May be worth donating.


Bonus: If you are sorting through a lot of clothes and have friends that may like your style, ask them if they would like to go through any of your items before you send them to other places. My coworker once was about to donate 4 bags of clothes to Goodwill. I asked her if I could take a peak and I would donate them for her whatever was left. I found some amazing pieces that I ended up adding to my closet for free.



That's it! You are on your way to a more functional and intentional closet this year.

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