On another thread, Mae wrote:
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My biggest problem - and there are many- is the "I might wear this again if it is... tailored... mended... worn underneath something" pile. I hate this pile because I *never* get around to tailoring or mending or wearing underneath. I am also reluctant to donate things that I *might* wear again (but haven't). So I end up hanging onto things. Just in case.
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The first thing I will say is something you already know: you will never tailor or mend or "need" those items. Put them in a black garbage bag (black so you can't see through it and start second-guessing yourself) right now and put it in the trunk of your car. Next time you pass a Goodwill clothing donation box, drop it off without a second thought. It will be such a relief to have them gone and no longer creating the burden of feeling you must tailor/mend/wear things you don't love.
Holding onto mediocre stuff out of this kind of anxiety will keep you from ever having a fully functional wardrobe. Trust yourself to be able to provide what you need. If you find that you're panicking twice a week because you don't have a black cami and you donated one that was too short or too faded, we'll find you a new one.
If releasing it to Goodwill gives you palpitations, try Angie's "hidden holding zone" method: http://youlookfab.com/2010/07/.....ding-zone/
Who else has advice on closets?