This is the one thing I've been good at tracking (well sort of, I gave myself amnesty for a small closet of things bought prior to this year as they were already sunk costs - although they have to pass the wear or purge test and I do track wears).
My goal is $2 on everything bought new this year by the end of 12 months, with $1 what I want to eventually get to. So far the less I have of something (bags, shoes, jackets) the easier it is to get down CPW. I have one leather jacket which might take awhile longer though as I avoid wearing it on rainy days. I know I like variety (so far this year I've worn about 170 different items of clothing - counting tights, shoes and accessories), but that too much is too unmanageble, and because right now I have so many tops it's hard to get down to $2 per wear for even very inexpensive ones.
The flip side is that once I'm below 1$ I feel like I got good use out of something if I then decide to purge it.
Carter - for me, it's part of the purchasing decision. I returned something I liked a lot because I didn't think I'd get the CPW out of it. I saw myself wearing it maybe 10 times a year at most. On the other hand, it made me realize that I could spend more for what was essentially my second 'real' bag, because I'd be carrying it about 40% of the time I left the house. It's also made me reluctant to buy any tights or hose over 10$ with 5$ or under as my goal, because they just don't last that long before looking ratty or laddering.
