Having been doing the mother of all culls (or 'editing my wardrobe' as I prefer to call it) for some time now, and having had one or two regrets like Laura mentioned, I have now come up with a no-regrets editing method that might work for some.
In my case, the problem is that I have loads of clothes that are high quality and that I love, and that fit me, and that are now, etc. I simply have TOO MUCH STUFF. This = a lot of scope for regret.
So here is what I am doing now that I have thrown out everything that obviously should be thrown out (polyester, stuff containing elastane or spandex, anything in poor repair etc): when choosing what to keep and what not to keep, I categorise the 'what not to keep' into various categories, pack each category tightly into boxes, and list every item in each box and each category. The categories are my speculative theories about which sorts of things I will definitely want to get rid of when I no longer have the storage unit I currently have (which is not cheap, so I really should get rid of it!). My plan is to keep the boxes for a year before finally donating them. This gives me a bit of leeway to allow for medium-term changes of mind, but is a definite step forward towards getting rid of stuff.
Ultimately, I do want to do a severe edit, both of my clothes and my books. I just have to do it, and move on. This method helps. Incidentally, in doing this, I have ended up actually getting rid of more stuff without waiting the year, when I see how many boxes of clothes and books I have waiting to be donated.
