I came across this post on a winter wardrobe on the Project 333 website which had a couple of tips in the comments that I found interesting:
Michelle says:
... The last thing I wanted to say was that I have always lived with overflowing closets. I don’t over buy, but I never get rid of anything. It’s always a drag to get dressed. Trying to start Project 333, I started off by pulling out anything strictly for summer or things like my xmas sweater, plus stuff that doesn’t fit but I don’t want to get rid of it. I know I need to deal with those later, but I found that after I pulled half my stuff out and put it in tubs, I was left with basically my most favorite clothes and my least favorite clothes. It suddenly became easy to grab things I didn’t want to keep and toss them in a giveaway box. ...
Rinna says:
I keep a basket near my clothes rack, where I put any item of clothing that feels even a little boring or hasn’t gotten used in a month or so. I call it “the rest basket”, where those clothes can take a little rest. I think it’s better to hide them from view, than look at them every morning and allow the bored-ness grow stronger. When I dig then out again, they feel somehow refreshed (or if they don’t, then it’s time to let go of them).
C. Emerson says:
... When I was first packing all the clothes not currently in rotation I separated it out into too small clothes, and likely to be donated clothes. I’m giving myself six months before the first donation time. For every week that I don’t stick to my goal of eating and living more healthy (and naturally shrinking in the process), one item goes from the too small box to the donation box. I don’t know exactly how it will turn out just yet, but I find its surprisingly freeing, knowing that when I hit my donation time either I will be close to fitting in to most of these clothes and they might show up in next quarter’s rotation… or… that somewhere along the way life became more important than a size, and I’m willing to let go of them.
I like these approaches to separating out what is working from what isn't, and the various ways of creating a "holding zone" and then weeding it out. The last one in particular intrigues me -- if a person has a goal of changing their health habits and hoping to lose weight, it can be a good motivator to have a system for getting rid of the physical items that don't fit. Provided, of course, that you can see it as a gift of liberation (and an acknowledgement that your actual life is more important than your size) and not a punishment for failure to lose weight.
For me, I am slowly realizing that the drive to keep clothes that are now too small is truly a way of punishing myself for being fat and gaining weight. At the same time I tend to see getting rid of things that don't fit as taking things away that I don't deserve, sort of how you might take a child's toys away if they don't keep their room clean. It would be nice to shift my perspective so that I can see getting rid of things as a process of setting myself free instead of depriving myself.