For various reasons, we all tend to hold on to clothing that makes us look fat, isn't our color, doesn't match anything else in our wardrobe, or is just plain ugly. Here are some guidelines to help you shed the garments that you don't ever wear but can't seem to give up.
1. Assemble a pen or marker, some Post-It notes, large garbage bags, and cardboard storage cartons. If your closet's not totally jammed, it's best to work through the contents while they're hanging up; surrounding yourself with piles of clothes can make the job seem even harder than it is. First pick out the stuff you know you know you want to keep, such as work clothing, and outfits you need to have for specific occasions like weddings, funerals, formal parties, or church events. Push those to one side of the closet.
2. Next, pull what you know you want to get rid of, the stuff you can toss without even thinking about it. This should include items that are way out of style, stained, torn, or hopelessly shrunk. (You may want to cut some of these up to use as rags or for sewing projects. You can turn shrunken wool sweaters into gifts.) Toss the rejects into the trash bags or boxes, but don't throw them out (more on that later).
3. Now the hard part: those maybes that you feel you should dump but, for whatever reason, you can't let go of. Take the Post-Its and, for each item, write down the problem with the piece ("It's hideous and it makes my wrists look huge.") and the reason you want to keep it ("Could be a great Halloween costume.").
Once you're finished tagging, leave the clothing alone for a few hours, or even a few days. When you return and review your notes, you'll have better perspective regarding what to keep and what to get rid of. If you're still struggling, ask a friend to help you make choices.
4. For vintage pieces or family heirlooms that you don't wear but can't bear to lose, consider putting them on display in a frame or shadowbox, perhaps with a photo of the person it once belonged to. Regifting may also be a solution, if you know someone close to you who would enjoy the piece. If you love something but will never wear it again, take a photo of it and write what it meant to you, and add the photo and notes to a wardrobe journal.
5. Important: Avoid throwing out your wardrobe rejects whenever possible, to keep trash out of the landfills. If you can't repurpose the clothes as described above, give them a chance at a second life: Donate them to Goodwill, sell them on Ebay or through a local consignment shop, give them away on Freecycle.org.
More: Gorgeous Storage Solutions to Control Your Clutter