This can be a surprisingly tough job. On the bright side, since I'm looking significantly better than I have in years, it wasn't as ego-crushing as the opposite--"I will never fit into this again..."--can be.
I had some simple ground rules--no sentimentality and no grandfathering. I don't care who bought me that shirt, it's six sizes too large now. I don't care how much that cost when I bought it, I don't get the money back if it sits in the wardrobe. I don't care that that looked fantastic on me six months ago/two years ago/in college. If it is not currently capable of causing a riot among the opposite sex,* it is not worth keeping around. Yes, there is a chance that I'll gain some weight back. There's also a chance that I'll lose even more. Let us not weigh ourselves down with possibilities.
In the event of indecision, if I haven't worn it in six months, it can go find a new home.
I allowed myself three ancient t-shirts for lounging, yard work, violent illness, and the chance that I get into a mad paint-flinging jag for awhile. This is the only indulgence.
Three and a half garbage bags later, the closet is much emptier. Tomorrow, I head off to Goodwill.
The appeal of minimalism is starting to grip me in a big way. I will never get down to pure Zen simplicity--I'm an artist, I require a certain amount of stuff to do the job, and anyway, I have all this art that I'm not willing to part with--but editing down my possessions as I have been lately is an oddly freeing experience.
*I lead a rich fantasy life, in case you haven't noticed...