Do you know how long an item typically lasts in your closet for? I've been tracking my purchases for almost 3 full years and as we wind up the third year, I'm noticing that I remove approximately 5 items from previous years, and for two main reasons: I've worn them to death, or they don't speak to me the same way as they did when I first bought it.
Thankfully, so far, none of my 'investment' pieces have fallen into either category and are still going strong. That's great confirmation that they were money well spent - phew!
Before I started tracking, I had a lot of clothes from many, many years ago and I used to think: "Wow, my clothes last a long time." Actually, what was really happening was I had a lot so they barely wore out and since I had so much, the ones that I didn't really like got lost in the pile, and I didn't scrutinize them as thoroughly as I do now for items that were looking old. In reality, there were a lot of items that I kept well passed their prime.
I'm a little bit more particular now about letting things go - if something looks too shabby for work, then I will designate it primarily for weekend use (which has actually made me look a lot more put together on the weekends), and if I don't feel the same about something any more, the chances of me changing my mind are now pretty slim that I can confidently just let it go without wondering if I'll have regrets. It's quite freeing and during this time that I'm not supposed to make any more purchases, it's been awesome for keeping my numbers down to a minimum.