Cleaning out your closet can be stressful. You want to throw stuff away, but something always holds you back. Why? Because clothes aren't just things you wear, they are how you express yourself, which means they're loaded with all sorts of meaning and significance that goes way beyond what they look like. That said, if you don't want to end up on one of those hoarding TV shows, you're going to have to put emotion aside and make some tough calls.
So, as you begin to assess the contents of your wardrobe, ask yourself the following questions (and beware of rationalizations that might derail your progress):
1. Do you like it?
Yes: Move on to No. 2.
No: Get rid of it. Donate it to charity, or, if it's nice, you can try selling it online or at a consignment shop.*
*Rationalization Hazard: "I don't love it, but it's still a good thing to have." Why? If you don't love it, you're never going to actually want to wear it. It will just take up space and contribute to that I-have-nothing-to-wear feeling that turns getting dressed into a chore, instead of a pleasure.
2. Is it stained?
Yes: Figure out if the stain can be easily removed. Is it just dirty, or is it ruined? Is it really worth taking it to the dry cleaner and paying to have them take a crack at it? Are those underarm stains just temporary or are they baked in at this point? If they're set, you have to say good-bye.*
No: Move on to No. 3.
*Rationalization Hazard: "Oh, whatever. No one will notice. It's just a little deodorant under the arm/pen mark on the sleeve." In that case, take it to the dry cleaner and see what they can do, but if they can't fix it, throw it out. The truth is, if you can see it, so can everyone else and even if they can't, do you really want to be wearing soiled and stained clothes anyway? You wouldn't buy it with a stain, so why keep it with one?
3. Is it faded?
Yes: Get rid of it.*
No: Move on to No. 4.
*Rationalization Hazard: "It's still a good thing to hold onto. I can just wear it around the house." Even if you love nothing more that to lie around the house in faded old T-shirts and shorts, you probably have one or two that you wear all the time and the rest are just taking up space. You don't need 20 lounging T-shirts. Nor do you need six not-quite-black LBDs. You just don't. Let them go.
4. Is it pilled, torn, or fraying?
Yes: Determine if you or a tailor can easily fix the problem. If you can, then move on to question No. 4 and remember to set it aside at the end of all this so you can take it to get repaired. If it's not an easy fix, you need to let it go.*
No: Move on to No. 5.
*Rationalization Hazard: "I'll get around to fixing it eventually. Just not right now." Be honest with yourself. If you are not going to take the time to fix it or spend the money to have someone else do it, you need to let it go. Period. Fabric shavers are a cheap and effective way to remove pills from sweaters, a tailor can easily repair rips along a seam, and it only takes a pair of scissors and a few seconds to clean up a frayed edge, but if you're not going to do it, you're not going to do it. Just let it go. No one will ever know.
5. Does it fit?
Yes: Move on to No. 6.
No: Get rid of it.*
*Rationalization Hazard: "It used to fit/it sort of fits." If making something fit is just a matter of bringing it to a tailor and having it taken in a little here or there, then fine. But don't hold on to clothes that are too small for you or that have serious fit issues that cannot be easily dealt with. It doesn't matter if it's new, if it cost a lot of money, or if it is the trendiest, coolest thing on earth. If it doesn't fit, get rid of it!
6. When was the last time you wore it?
Less than one year: Keep it! It's in great shape and you're still using it. In fact, you'll probably wear it even more now that you don't have so much other junk clogging up your wardrobe.
More than one year: If you get all the way to question No. 6 and realize you haven't worn the item in question in more than a year, don't throw it away; set it aside. Fold it up, put it in a plastic bag to protect it, and store it in a box or a drawer or under the bed. It's still a perfectly good piece of clothing. You're just obviously not that into it right now, and that's fine, but there's no point in keeping it out in plain sight if you aren't wearing it. Put a sticker with the date on the bag and wait six months or a year and reassess. Either you will start wearing it again, or you will realize you really aren't into it anymore and you can get rid of it.*
*Rationalization Hazard: "I don't need to store it. I know I don't wear it that often and that's enough." No. It's not. You need to not see it for a while to figure out if you really like it or not. Trust me. Put it away. You're not getting rid of it. You're just taking it out of circulation so you can focus on the amazing pieces you actually do like and wear. If that means you are left with just 15 pieces of clothing, so be it. You probably only really wore those pieces anyway.