It's frightening to get rid of pieces of yourself. That's what it feels like when I go through my wardrobe in preparation for packing. The great purge - I should have done it before I moved to the Bay Area from Phoenix, and honestly, I did get rid of quite a lot of things before moving, but it feels like I didn't make a dent. My current closet is the size of three regular size closets. Still, I have a full dresser. Christian's closet is much smaller and half the things hanging in it are uniforms - that he doesn't own - for his job.
Clearly I'm the one who has to purge my clothes.
So I asked for advice. I read organizing articles. I took my clothes out and put them in three piles - yes, no, and maybe. Already one garbage bag is ready for good will - but it was hard for me. The concern that had been keeping me from the purge was the idea that my old clothes would fit me again once reaching my fitness goal. As it is, some of my old clothes do fit, but the reality is that a lot of the leftovers are just not worth moving. It's better to reward myself with new clothes when I'm svelte than holding on to things which I may never want to wear or may never fit again. Fashions change and so do tastes.
Once I had gone through my clothes I moved onto purses, jewelry, and hair things. It was a lot easier because I had already done gone through the process with my closet (the first round anyway). Not only is it better to get rid of these things because I'm not using them anymore, but also because it declutters my living space. Beginning was painful, but by the end, it was cathartic. Even if you're not moving, I recommend going through the process. I love having empty space in my closet again!