I go through my closet every year and get rid of things. In recent years it hasn't been because of weight loss, though. I try to be tough with myself and get rid of anything I haven't worn in a year or more, regardless of how much I like it or hope to fit back into it one day.
Now that I
am losing weight, I will be sure to get rid of all the billowy, "flattering," tent-like clothes I have. I will be HAPPY to do it!
However, I think I will hold on to at least one outfit, so I can try it on from time to time. It's a big morale boost for me to wear baggy clothes that used to be just right (or almost too small) for me.