2-Does it still fit?-Okay so I am usually a size 6-8 I have a few clothes that are one size up and one size down, but not a ton of them. Mostly a couple pairs of jeans and slacks. I put them in a bin in storage marked with what size they are and you bet you I remember they are there when I get to that size (well, maybe not when I go up...not as fun for sure). A few years ago I was a 0-2 that isn't going to happen any time soon and if it does, it isn't worth holding onto the clothes that will probably be out of style anyway...get rid of them.
3-Is it still in style-Okay this is a tricky one, because things do go in and out of style so quickly. I don't usually spend too much money on fads so I don't have too hard of a time getting rid of things once they are out of style (I hold onto them until they are good and out :) I do however have a seriously awesome Ralph Lauren skirt that the second petticoat skirts ever come back in style, that thing will be on me! But I really don't keep many of these things, and if I do, they go in a bin waiting for the day they will make their debut once again.
4-Do you love/strongly like this article of clothing? Most of us are always buying clothes (some more than others). There are only so many days in the week when you can wear what you have. I have a huge love of skirts and I realized that I had more skirts than I could ever wear in a year of Sundays. Most of them I LOVED but some of them I just thought were okay. Every once in a while, when I buy a new one I love, I replace one that I only sort of like giving the old one to a thrift store. It helps with attachment issues. This is always changing for me. Something I can adore one year, I might not love so much the next, I get rid of it when I don't love to wear it anymore.
Obviously I am not head over heels in love with everything I own, but I I try to do the "replacing" thing when I find new things and it does help me to get rid of things I don't love as much.
5-When is the last time you wore it? If I haven't worn it in a year, I donate it. If you are really going to push it, try a year and a half to two years. If you haven't worn something you own in that long, you probably don't love it and won't miss it (I promise you probably won't think of it after it is gone). Think of it as freeing up a hanger for something you do like :) If you really love it but don't wear it, but it in a bin, don't leave it in your closet (sometimes when you have a bin full of unworn clothes, it is easier to get rid of...baby steps.)
When to keep things-
1. Classic pieces-Things like black pencils skirts, cardigans, white button down shirts, wool coats, LBD, classic style boots, etc. I usually spend a little more on the classic pieces that I add to my wardrobe. When these pieces fall into disrepair, I get them fixed because they are an investment and I want to use them for as long as I can. I only get rid of them once they are unusable (holes that can't be fixed, discoloring etc.)
2. Sentimental pieces-I totally get there are pieces that you want to keep forever. Your wedding dress, a special bridesmaid dress, graduation robe...I am keeping my dress I won Mrs. Utah in. It is special to me and has good memories attached. Just be careful of this one. The shirt you wore on your first date with your ex-boyfriend, the dress from spring break of your senior year, the holey sweats with the word "flirt" across the rear, should all probably go (at least don't go out in public with the flirt sweats unless you are 13 years old...just a little bit of friendly advice :).
A couple members of my family have done something really fun with sentimental shirts that they didn't want to get rid of. My mom made a quilt for my brother with all of the soccer uniforms he has ever had. My brother was the student body president of the university that he went to, his cute wife made him a quilt out of all of the shirts he got from different activities he did through college. There are ways to hold onto things without leaving them in your drawers/closet. I want to do this for my boys with both their sports uniforms and the school shirts we buy every year for spirit day. They are good memories and I think are okay to keep, in a bin or in a quilt or something out of the way.
3. If you love it! I will always keep those pieces in my wardrobe that I love. Most of them are pretty classic and I feel good in them. I don't always strictly adhere to wearing things that are on trend. I have a ton of full skirts that are flattering and cute, pencil is the skirt that is more "in style" right now. While I love a good pencil skirt, I am not going to stop wearing my cute a-line skirts as well. Your personal style is what you feel good in and what you like. If you feel like a rockstar wearing it, by all means keep it! But if you don't love it, or really even like it, and don't wear it-send it on. There is someone thrift shopping right now that might love what you donate.
I always try to ask myself if I would buy it again if I saw it in a store. If the answer is no, why keep it?
There is such a guilt for me when I have a ton of clothes that I don't wear, I guess that is good because it helps me keep my closet cleaned out. My sister was telling me that what helps her get rid of things is to have a yard sale. If it doesn't sell, she has already detached herself from it and she takes it all to the good ole thrift store. I think it is a good way to do it if you have a hard time detaching yourself from things. You can also try to sell it on ebay if you paid a lot and want to try and get something back for it.
I love having a closet full of things that I actually wear and are my size. It makes picking out an outfit in the morning so much easier and getting ready a lot more fun. Hope this helps!