This is an interesting topic
I guess the things that I will NEVER wear again would be the large, shapeless t-shirts that I used to wear. When I was heavier my wardrobe consisted of jeans, t-shirts and sneakers. I would "hide" under those things. I am now able to wear the stylish and trendy things I always wanted to wear but never could. I remember how terrible I would feel lost inside those layers of clothing while everyone else my age would wear the clothes that were in style. I never want to feel that way again
I guess that is why we are all here on this site - to help free ourselves from our prison of heaviness.