Here’s how I think of it. Stuff that’s too small: if I fit into it again, I’ll want to buy something new and celebrate anyway. Maybe keep one piece you’ll never find again, but you can buy more jeans and dresses. Stuff that’s too big: don’t tempt yourself. Stuff that you never wear: make room for stuff you love. Basically, if I pull something out of my closet, put it on, hate it and take it off, I get rid of it. My goal is to have only things in my closet that I can always wear. It makes getting dressed so much easier. Even if I only have 6 shirts, I can just pick whatever matches my pants. *Realizing this comes from the privilege of being able to buy more jeans and dresses, but I think we’re all there.