I just did a ruthless closet purge. I got rid of:
-the old and worn
-things bought on sale that I never wear
-unflattering tees I might throw in in a pinch
-dresses that are now too big or don't suit my style
-shoes that I originally bought because they were in my budget at the time, but have since replaced with something nicer
-short shorts and miniskirts from when I was a teenager

Sitting in my back seat right now are 5 garbage bags worth of clothes and shoes that were cluttering my closet, driving me crazy, and making it harder to get dressed. After work today I am donating everything that is still in good shape.

What I ended up doing was setting up a spreadsheet and listing out the different "capsules" I need in my life - work, casual, gear, dressy, beach, pjs, active/lounge - and listing the items I have that fit each, that I like and wear, from memory. It turned out that I have loads of things that I like and that work for me. Next, I went through my closet and ditched the things that weren't on the list. There were one or two items I had forgotten about that I decided to keep, but for the most part if it wasn't on the list it went. I think I have finally gotten my head around the facts:
-Even if it's only _____ dollars, if it's not great it wont get worn and is a waste of my time, money and space
-Keeping things that I don't like or wear just because they aren't worn out is a waste of my time and space
-Clothes don't equal memories

What a relief.

Now that I know where the few holes in my wardrobe are I look forward to filling them with fabulous things that fit great and posting pictures of my newly organized closet!