I've spoken to quite a few people over the years who say they have very nice clothes they love but the don't wear them anymore. But my question is this: If you value something so much...then don't you think you should be wearing it? The reality is we are a society who likes to accumulate and, dating back to the Great Depression, we tend to keep everything we believe has monetary value when, in reality, it really doesn't. For example, a pretty dress or a nice suit you bought ten years ago went for what can be considered a lot of money. And the problem is you haven't touched it in nine years because, as most clothes do, it went out of style. Could it come back in style someday? Maybe. Styles do often return. But this is not a reason to hold onto things you don't use..."just in case." You feel like, because you spent "good" money on it, you are throwing money away. But ask yourself this... is it putting money in your pocket sitting there in the back of your closet with dust on the shoulders? Is it giving you anything? Do you benefit at all from keeping outdated outfits? Now ask yourself one more question... will you gain anything by getting rid of it and donating it to charity? Of course you will! The benefits? More space to be able to keep the clothes you are going to wear (we only wear 50% of the clothes we own, by the way.) I might even suggest buying a new outfit for every three to five you get rid of. The purpose? Because new clothes make people feel good. I don't recommend buying new clothes for the sake of buying new clothes and throwing away your money. But you've got to admit putting on a new pair of pants that make us look better is a nice, uplifting feeling. The thing is the items taking up space, yes, you paid for them. But by keeping something you no longer wear or use you are not getting anything in return but more clutter and a lack of storage space you could be using for something else. Here is something you should do right now with items (they don't have to be clothes) you are holding onto because you paid good money for them. 1. Go find ten items you own for one reason and one reason only... because you paid for it. 2. Grab a piece of paper and make three columns. 3. Write the items you are having trouble getting rid of in the left column. In the middle column, write "why I am keeping this item" and in the third column write "what will I gain by getting rid of this item." My guess is you will have a lot more in the right column than you will in the middle. Be specific with both. If you can honestly fill up the middle column with more reasons of why you should keep it, and they are good, legitimate reasons, then maybe you shouldn't get rid of it. But I'm willing to bet that won't be the case.