8 Questions to Ask Yourself When Decluttering Your Closet

I started AALLYN because I believe in a more intentional approach to style: one that results in a streamlined closet filled with things I love and wear. For me, that ends up being timeless garments & accessories that are well-made, comfortable, and make me feel amazing. Though I have my closet figured out now, it wasn't always this way. I used to struggle getting dressed every morning because I had a closet full of things and nothing I wanted to wear. Since you're here, I also have a hunch that you relate to that struggle.

Please tell me if this sounds familiar: you want to declutter, but when you stand in front of your closet, you can't seem to let any of it go. And once your favorites are in the hamper, you're left sifting through a jam-packed closet, feeling like there's "nothing to wear." If this is you, I see you and have been there. I lived in this cycle for years before deciding that something had to change. Getting dressed was more frustrating than it should have been, and I was ready to do something about it, so I decided to declutter. The only trouble was that I had no idea where to start.

If you're reading this, that means that you know already know that decluttering clothes is hard. And that's because they're more than just clothes and accessories; they represent many things—everything from our hopes, dreams, and fears to our insecurities. I understand and have been there too. It took me a few years to go from wanting to declutter to making real progress. It took me so long because I didn't have a good system to evaluate my closet. I was always talking myself back into old habits, making exceptions, and my exceptions turned into dressers filled with things I never could figure out how to wear. I needed a way to look at my closet in a new light, so I followed a system that worked and started to see actual results.

So here it is - the eight questions that got me to declutter my closet successfully. These questions helped me see my wardrobe more clearly and gave me a good mental checklist to use when I thought about buying something new. I hope they'll help you as much as they helped me, so you can start doing more with less.

#1: How does it fit?

It seems obvious, but the key to remember is that fit is not just about size. We can all buy things that technically "fit" - the measurements are correct, and we wouldn't have bought the size up or down, but they might sag in the wrong places or be a little too tight in others. These details are every bit as important as the actual size of the garment because at the end of the day if it's ill-fitting, we're likely to skip wearing them even if they're cute on the hanger. These kinds of fit problems are often less about your weight and more about how the garment was designed. Remember: we're all different. If something doesn't fit the way you want it to, regardless of what the tag says, it's okay to let it go. The goal is only to keep things you feel great in, and if something fits poorly, that's the perfect candidate for the donation or sell pile.
That said, when it comes to being too big or too small, I take a realistic and practical approach. I'm not made of money, so if something stops fitting because my size has changed, I wouldn't automatically throw it out. I make a rule for myself that I'll keep it in a specific place in my closet and revisit it in X amount of time (for me, that's six months). I'll consider tossing it if it still doesn't fit by then. My body tends to fluctuate with the seasons, so this approach has allowed me to minimize without prematurely letting go of things I'll end up replacing in the future. Remember that you're not a "bad minimalist" if you decide to hang on to something, but make sure you're not keeping items just for the nostalgia of the size itself. 

#2: HAVE I WORN THIS IN THE PAST YEAR?

This one is pretty straightforward: if you haven't worn it in a year, you will not wear it. The only exception is special occasion items, but even that doesn't give total immunity. Not wearing something for a year means taking up space that should be inhabited by something you will wear and love to wear. Eliminating these pieces from your closet will make getting ready feel easier. On the flip side, clearing your closet with this technique may also help you uncover things you've forgotten about. It's like shopping in your closet! 

#3: WILL I (HONESTLY) WEAR THIS AGAIN?

This may seem straightforward, but this question forces us to be honest with ourselves. Are you going to wear it again, or is it outdated, a trend of the past, or generally just something that's no longer in style?
Asking myself this question is ultimately what led me to rethink my viewpoint on trends vs. timeless style. I realized that I was buying many things that were "good deals" but had trendy details that are here today, gone tomorrow. And they were often cheap feeling or bad quality, so I wasn't reaching for them often because they didn't feel great on my body. The mistake I was making happened at the point of purchase - in me, believing that a closet full of things I could wear today meant I was investing in my long-term style. Unfortunately, that was far from the truth. They weren't trendy pieces when I looked at what I loved to wear. They were styles I had loved forever and typically were my more well-made pieces. 

#4 IS THIS STILL MY STYLE?

This question elicited a lot of cringing and flashbacks to earlier, less fashionably evolved moments in my life. I don't know about you, but once I'm "done" with a style phase, I'm typically not going back to it again, or at least not in the same decade. If it was my style in 2010, it should stay in 2010, and I can revisit it through old photos. I don't need to keep it in the back of my closet just for the sake of memories. Please take a photo, put it into your donate/sell pile, and move on. I know many of us hang onto pieces hoping they'll make a comeback, and I believe in that for a few *special* pieces (jean jackets or leather jackets, for example). Still, I know it's a problem if you have an entire section dedicated to this purpose. Pick a few favorites, store them out of sight to reduce the clutter, and know that you've held onto them as mementos.

#5: Am I holding onto this because I feel guilty about its cost?

This one is so common. It's what I hear the most when I talk to my customers about their own closets and style journeys. We keep things we don't wear out of guilt because of the money we've wasted. 
I understand this feeling, and it's why I started my Poshmark journey - I was holding to recoup some of the cost from things that never saw the light of day in my closet. Regardless, I still get an anxious feeling in my stomach when I think about the money that was wasted over the years. It's not a pleasant feeling to face this guilt head-on. If you feel it, too, I know how tempting it is to give up on your decluttering mission and close the door instead.
But here's a different perspective: years of experience have taught me that the longer you wait, the worse that feeling gets. You're better off confronting it, and here's how I mentally overcame the feelings myself: Thing of the money that you spent as an investment in yourself. In your education and wellbeing. You made mistakes, but you're now learning from them and won't repeat them in the future. Give yourself the gift of forgiveness and move on into your new and wiser self.

#6: WOULD I BUY THIS AGAIN?

This is one of my favorite questions to ask myself when I'm evaluating a garment or accessory in my closet. If I walked into a store today and saw this on the hanger or shelf, would I grab for it again (ignoring any price regret since it's already been spent)? If the answer to this question is No, then it's not worth keeping. This is similar to the guilt question above - you may be keeping it just because you bought it in the first place, but you should treat the space in your closet like you do your money - if you wouldn't spend on this again, don't waste your closet space on it. 

#7: DOES IT COME WITH A "BUT"?

Don't evaluate your closet without trying on each piece. We often tell ourselves we love something but base this on how it looks on the hanger or on the shelf. It can often be a different experience once it's on the body. A quick check I like to do is, am I comfortable? Can I sit down, bend over, and reach for something? 
You should only keep things that feel good and comfortable as soon as you put them on. I pay attention to if I'm automatically pulling down on the hem, pulling up or adjusting the neckline, etc... Things that require constant adjustment or simply must go. This also goes for material - even if it looks great, we know how unpleasant it is to wear something itchy or clingy. Over time, you'll stop reaching for them because the experience of wearing them is unpleasant. Eventually, they hang there and become those pieces that give you guilt. 
The goal is to aim to fill your closet with items that make you feel comfortable in your own skin and that make you feel amazing. 

#8: HOW DOES IT MAKE YOU FEEL?

This is another favorite. Look at the garment or accessory and ask yourself, "does this make me feel confident and amazing?" If the answer is no, then ask yourself why. Why are you wearing it, keeping it, or allowing it to take up space in your closet if it doesn't elevate your mood, transform your feelings, or make you feel comfortable? I bet you can think of a few things in your closet that do give you this feeling, and if so, that means those will always be chosen over one that doesn't give 

All right, friends! Now that you're equipped with the methodology, it's time to put it into practice! They say that clearing your environment can have a similar effect on your mind, and for me, that's been true. By simplifying my wardrobe and being clear on what my goals are for my style, I've saved time and energy every day because I no longer am rifling through drawers and hangers to find the 20% of my closet that I actually love and want to wear. I no longer have skeletons of past impulse purchases hanging in plain view, haunting me. I can walk up to my closet, reach in, and know that anything I pull off a hanger will work. That feeling is so freeing, and I hope to be able to help you achieve the same. I hope you've enjoyed these tips and wish you luck in your decluttering journey! 

xx
Allyn

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