Luckily, it's really easy for me to let things go (YAY, I'M NOT A HOARDER). I throw anything I haven't worn recently into a pile to reevaluate in a month or just donate. I'm even guilty of hiding the beau's unworn shirts or his shrunken jeans. No one needs over thirty comfort shirts. No one. If it's been over six months and he hasn't looked for them, I'll ask him if I can donate them to a Naked Lady Party*. The girls love his clothes.
Today that pile turned into a gigantic garbage bag filled with some unloved but mostly loved clothing. Sometimes it's like breaking up with someone. It's not you, you lovely hot pink Betsey Johnson dress, it's me. It's not that I don't like you, I've just changed. I need to move on. There are plenty of other ladies in the sea. You'll find a companion again.
*Naked Lady Party (aka Switch and Bitch) is when you gather up unwanted clothes, get together with your lady friends, throw everything in a huge pile and take whatever you want. You see it first, it's yours. It's awesome.