How much of your closet and/or dresser is clothes you actually wear? If you are anything like I was, maybe 50% at best. How many times do you open your closet doors, stare at what you have and think "I don't have anything to wear!"? You have plenty of clothes, just not things you want to wear. How do you let go of things and make room for clothes you will actually enjoy wearing? It can be a tough process.
Here is a flow chart I use to organize and let go of clothing:
There are other relevant questions that aren't included in this chart. When you get to a "No" and you catch yourself saying "No, BUT..." one of these questions might apply:
1) Does it need repair? Yes ► Does it cost more to repair than to replace? (Yes► Discard!) Will you get it repaired in the near future? No ►it isn't important enough to keep!
2) Is it a sentimental item? Yes ► Pull it out of your closet/dresser and set it aside. (I will address sentimental items in a blog post soon). No ► it isn't important enough to keep!
3) Not sure if you've worn it in the last 3 months? Try this:
When you have gone through your whole closet and completed the first round of purging, turn all of your hangers backwards. As you wear/wash items turn the hangers back the right way. Then set a date in the future (6 months is frequently recommended, I personally do 3 months to ensure I keep up my motivation/commitment to the purge) that you will re-evaluate. Any hanger that is still backwards at that point in time goes back through the flow chart.
I always find that I say "No, BUT.." less after it is really clear that I haven't worn it in 3 months. You can do a similar thing with your dresser by folding clothes differently, putting them upside down, etc..
I also set rules for myself regarding keeping clothes. When I buy new workout pants, I have to get rid of a pair that are damaged. I only keep mismatched socks through the next wash cycle (if it didn't turn up by then, it probably won't).
It can be especially hard to get rid of your own clothes. Sometimes having a friend or professional organizer there to assist makes it easier. The same reasoning/excuses that you accept for yourself may sound ridiculous when your helper repeats them back to you. (There is 0% chance that I'll fit into my high school prom dress again, nor have an occasion to wear it. There is no reason to have more than a week's worth of black t-shirts.)
If all else fails you, remember the room you'll be making for new, fun outfits that you will actually wear! Or call me and I'll be the tough-love part of the equation. :)