Your post sounds like What Not To Wear. Empty out the closet and educate the fashion deprived person. The first time I watched that show, they featured a woman my age. As they went through her closet, I couldn't believe how many things in her closet were just like the things I have in my closet. I paid attention to the tips and although I still have trouble letting go of some things, I am a whole lot better. I do let things go more readily now. An intervention is sometimes the only way people find out they need to change.