6 Questions to Ask to Know what Clothes to Keep or Let Go
I don’t know about you, but I love the calm of the very beginning of the year. Don’t get me wrong—all the festive holiday decor gives me the warm and fuzzies all season long, but once the calendar page turns, I want to feel zen, not in a constant state of visual (and mental) overload.
One of my favorite places to do a calming reset is the closet.
Most of us have far too many things jammed into our closets. It makes sense—no one else sees our closets (they’re our own private shame.) However, all that visual clutter leads to mental clutter. It’s a guaranteed way to start your day frazzled, frantic, and anything but confident.
Why do closets get so out of hand?
Sometimes it takes years to really realize your own personal style, and then our style as well as our bodies and lifestyle changes over time. Meanwhile, we have to wear clothes (it’s the law), and our closets become bloated with clothes that don’t reflect who we are (much less who we’re trying to become.)
In an ideal world, you’re curating your wardrobe quarterly, each time you rotate your clothes for the new season (you should be doing that, too), but we all know that’s not always realistic. Sometimes you just don’t get around to it. That said, even when you do set aside some time to detox your closet, it can be hard to know what you should get rid of and what to keep.
While I can’t help you make time to clean out your closet, I can help with knowing when it’s time to ditch an item of clothing.
Evaluating your Wardrobe
First things first, take everything out of your closet by category. I recommend this order: tops, bottoms, dresses and one-pieces, outer layers, shoes, and then accessories. That said, the order doesn’t matter as long as it’s one category at a time.
Put on each item of clothing, one by one, and evaluate it in the mirror. Ask yourself the following questions.
Tip: Before you even start, you should get fully ready. Put on a normal amount of make-up and do your hair how you would on an average day.
If you’re new here, I’m Missy of Simplified Wardrobe, an Ethical Personal Stylist & Capsule Wardrobe Curator. I help ambitious and eco-conscious womxn who want to look great, feel confident, and simplify their lives.
Find more information about personal style, capsule wardrobes, and color analysis over on Instagram. You can also download my free 10-page Guide to Defining your Personal Style.
6 Questions to Ask When Getting Rid of Clothes:
1. Does it fit?
When I say “fit” I do not mean “zip.” I can get a lot of clothes physically onto my body with enough effort, but that doesn’t mean they fit. You know if it doesn’t zip or button easily, but even if it does, it still might not be the best fit. Look at it objectively from every angle.
Make sure it’s free from any pulling, pinching, or bulging.
Make sure it’s actually comfortable and you don’t feel like you’re about to burst
Make sure you can sit down, raise your arms, and walk without riding up or ripping a seam
If not, it’s time to donate or sell.
If you fluctuate pretty widely during your natural menstrual cycle, then you can keep some things that fit only during that time, but I caution against saving any “someday” pieces or anything in a size, either larger or smaller, that you haven’t been in years.
2. Does it look good?
This has more to do with how you feel in it than any societal beauty standards. Take some time to figure out what styles, cuts, and colors you like to wear. I wont ask if it’s flattering but rather, do you like the way you look wearing it?
Take your measurements (at least your shoulders, bust, waist, and hips), and learn about how you can use clothes to manipulate your shape. The more you know about how different elements of clothing interact with your body shape, the better you’ll be at picking and putting together clothes to look however you want to look.
Figure out which colors bring you joy and also which colors and color combinations make you look and feel your best.
Knowing what makes you feel and look your best will help you evaluate the clothes you have now, and (bonus!) it makes it easier to shop in the future.
3. Is it in good condition?
If it is stained, ripped, or frayed beyond repair, it’s time to go. If aggressive washing has left it threadbare or shrunken, it’s time to go. If moths (or pets or toddlers) have left if holy, it’s time to go. Anything damaged beyond repair should not take up space in your closet.
That said, some damage can be repaired. If it still fits and looks good and you think it can be salvaged, then set it aside to be repaired. If it can’t be repaired, then it’s time to throw it out or repurpose. You can turn old t-shirts into rags or see if you (or a tailor) can save the skirt of a dress and fashion it into a stand-alone skirt. If it’s possible, it’s better to repair or repurpose a damaged item than to donate it damaged. That’s because they often wont get sold, and it will end up in a land fill anyway.
Be really honest with yourself. If you know you’re never going to sew on that button, consider if it’s worth hiring someone to do it for you. It can be easy and worthwhile to gather a lot of small repairs at once to take to a tailor. Small repairs are usually pretty cheap, between $3-$15 depending on what it is. However, if you don’t want to spend even that amount of money, it’s probably not a piece that’s worth keeping.
4. Does it make sense for your life?
Be really honest. Consider what activities you do regularly and what you need to wear for each of those activities. If you usually wear jeans and t-shirts, does that bright red suit really make sense to keep? If you’ve never once worn a skirt to work, are you going to start now? For special occasion pieces, ask yourself if you would be thrilled to wear it when that special occasion comes around. If you’d probably opt for something else or shop for something new, there’s no reason to keep it.
One caveat here. Sometimes we hold onto items because they’re what we WANT to be wearing, but aren’t for some reason. In this case, consider if it would be possible to wear the item on a regular basis—as in, it’s not against a strict dress code and it wouldn’t impede your daily activities. If the answer is yes, it would be possible, then think about what’s holding you back from wearing it now. Maybe you just need to figure out how to incorporate it into an outfit. If the problem is that it feels out of your comfort zone, maybe there’s a “training wheel” item you could start with to test how you feel (like a colored jean or palazzo pants). On the other hand, you could just dive in and go for it! You might be surprised that it doesn’t feel that weird and you’ll probably get a positive reaction if you feel great wearing it.
5. Does it match who you are today?
Like I said before, it often takes us years to develop our sense of personal style. If your personal style isn’t as defined as you’d like it to be, I have a free guide that will walk you through the steps of figuring out your ideal Signature Style.
That said, our style is constantly evolving based on our own taste and experiences, our environment, our age and stage of life, our career, and a myriad other things. Sometimes we hold onto pieces that remind us of who we used to be but don’t really serve who we are today. This is not about “dressing your age”. If you still your club clothes from your early twenties with no abandon, then go for it! I know for me, there was a point at different stages of my life when a lot of the old clothes I used to love no longer felt relevant for who I was today. I see this in my client’s closets a lot, too. Sometimes they can even hold us back. Those pant-suits that you wore just out of college might still fit fine, but they remind you of being a new grad. They don’t make you feel like a the powerful Senior Manager, VP, C-suite exec, etc. you are today.
Nostalgic or sentimental items can be the hardest to get rid of. I get it, too. Getting rid of our cherished clothes from an early era in our life can feel like giving up a piece of our identity. If saying goodbye is difficult, I recommend finding a box, bag, or bin that you can store the items in out of sight. If you forget about them and don’t reach for them in 3 (or 6, or 12) months, you can be pretty confident that you’re never going to. For some closure, you can thank the items for being with you during that time of your life and send them on their way.
6. Is it your style?
Now, a neutral basic that you need to make outfits may or may not fit a certain aesthetic. In that case, you can be happy that it fills a hole in your wardrobe. For more statement-making pieces, make sure it’s a statement you want to be making. Sometimes we have items that fit well, look fine, and make sense in our life, but we just don’t love them. Often these are items that are in mint condition (sometimes we’ve never even taken the tags off), but we still aren’t wearing them because we don’t love them—they’re no longer (or maybe never were) our personal style.
Don’t keep anything in your closet that you don’t love just because it was expensive. I know it hurts to get rid of something with tags, but it only hurts once, then you forget about it. When you keep it hanging in your closet taunting you, it hurts everyday time you look into your closet. It makes you feel foolish and dumb to have wasted the money. I get it. I’ve done it too. Feeling bad doesn’t get you the money back, but selling it might (at least some of it, which is more than you have now.) Also, you have the gift of a lesson. You’ve learned what’s NOT your personal style, so you won’t make the same mistake next time.
Once you see your perfectly culled closet with only things you love, you might start to see patterns. Get curious. “Huh, apparently I really like to wear green. Interesting. I seem to look great in pencil skirts. Noted. A lot of my clothes are tailored. I must like that aesthetic.” The more you do this, the more clear you get on your style so the next time you’re out shopping you can ask yourself “Does this make sense with the rest of my closet?“
Need more help defining your signature style? Want more help? Get your free step-by-step guide to discovering and defining your Signature Style.
Want even more tips for a successful closet detox?
Professional organizer, Carly Adams, and I created a free guide to fully edit and organize your closet. We’ll give you all the tips and tricks we use with our clients.
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