Peter Walsh--the guy from Clean Sweep, author of It’s All Too Much--offers this tip for cleaning out your closet:
After you’ve done a major purge of your closet, remove all the remaining clothes that live on hangers, and put them back in backwards, such that the open end of each hanger now faces you. Got it?
Then, mark your calendar for six months (or whatever) from today, and go back to your business as usual. Except that after every time you wear a shirt or a jacket or a skirt or what have you, when you replace the item, make sure the hanger faces the opposite/usual way (with the opening in the back).
When your six months have passed, and your calendar reminds you that it’s time, open your closet and remove every piece of clothing on a backward hanger; the chances are good you can give it away without the slightest pain, because you just clearly demonstrated that you don’t wear it.