I had mixed feelings: some things I really liked (e.g. soft v-neck sweater in both true red and purple I got from Fatsionista Exchange), and I'm hanging on to those for when I want non-confining clothes. But when I was trying to buy clothes at thrift stores in my size when I weighed 315 lbs., it depressed me how few nice things there were in my size. Now I smile to think of a woman that size (or a man with gender issues) having nice things for not much money. FLYlady calls it "blessing the world."
I'm paying $$ to have a size 22 red satin Calvin Klein dress taken in because it's the first piece of clothing I bought after surgery and although, in theory, it must exist in my present size, I can't seem to find it. But I love that it's the size I wore when I was a newly wed/young mother, and now it swims on me. (Also another Fatsionista Exchange buy.)
Usually for fat women finding a delightful piece of clothing is the end result with hunting and several bouts of being disappointed. Sometimes a piece of clothing is a victory. Giving it away is like giving away a trophy.
One hint: I organize my clothes in the closet by color (too many times I've work a suit with navy pants and a black jacket). I took note of the biggest chunks of color and used them to guide my shopping. My "colors" are red (pink, magenta), blue (teal, turquoise, navy, aqua, royal blue), purples, and black plus a few multi-colored prints, white pants, white tank top, etc. Plus denim. Not many women get a change to create a style from scratch, so I try to focus on that to balance saying good-bye to the old stuff. Also, Google has an application where you can find images of details you liked in your clothing and find new stuff that incorporate that detail. You wouldn't believe how many empire-waisted dresses with a sweetheart neckline I've looked at trying to find my dress!
HW (2005) 320; Pre-NoS 298; SW (2010) 265; SurgWt: 257, CW: 210.2