I've lost over 170 pounds and had to go through this process about 4 times. I just bought inexpensive clothes and very few at that, had to do the wash them a lot and when moving on to the next size I threw out the "personal" items and donated the clothes to charity. As I reached my goal weight I invested in a few more costly items and have kept them. I find that I wear a medium-and-a-half in tops or S-M-L sized stuff which of course doesn't exist so I wear larges and enjoy the extra room, a few items I can fir in a medium if it's cut larger.