I usually make note to do this once or twice a year, simply because I keep more clothes than I actually wear. I think a lot of times we get caught up on the amount of money we spent on a particular item. If we spent more on it, even though we don't wear it, we feel obligated to keep it until its value has worn off. Barry Schwartz in his book "The Paradox of Choice" calls this "psychological worth" or value. I believe the general rule of thumb when rummaging through your closet is that if you haven't worn it in the past two years, you probably won't be wearing it again. Don't be afraid to put it in that recycling bag, remember thats its going to someone who will actually use it.
Going through my closet I came out with a trash bag full of clothes. Luckily, the day that I cleaned out my closet, I went to get my mail to find this in my mailbox.
Its a postcard asking for clothing donations for a local charity, in this case, the epilepsy foundation in my area. You may get these in your mail occasionally, and whats great about them is that they have a date they will come down your street, and all you have to do is put your donations on your curb, and they'll pick them up. Easy as that! Even if you don't have this type of thing going on in your neighborhood, there can always be donations made to Goodwill or the PlanetAid bins that you may have in your area (or something similar).
As you may read from a previous entry, trying to sell your clothes (I tried Plato's Closet) can be quite difficult. I brought almost two full boxes (and I am talking LARGE boxes) and they only took three or four things for fourteen dollars. I also looked into a local consignment shop, only to be slammed with some pretty hefty criteria (for example, having $50 worth of items on their floor, and non-seasonal items). These options make sense if you either have a lot of recent clothes that have been only worn a few times, or you have a larger family that also goes through a lot of clothes. Otherwise, I would recommend simply donating used clothing. There doesn't always have to be "something in it for me".
Anyways, in attempt to better organize my closet, I organized all tops by color, rather than style (somewhat, although for the most part I just put things in random spots). Even though you may not find practicality in it, it certainly makes your closet more rainbow-like with all the colors separated. What I also came to find was it was easier for me to match tops together when they are categorized by color. Supposedly the theory also goes that it is much easier to find a matching top with whatever your bottom is when you have all colors in one area. I'll keep you informed as to if this theory is actually helpful.
If you have some time, go through that closet. I get a great sense of relief by freeing some space in my closet, getting more hangers back, and hence making the choice of what to wear easier in the morning when your fashion sense may be less up to par.