I originally started writing this as a response to Sterling's recent post about whether to keep some particular items during a closet purge. Ultimately, I decided to start an additional thread, with credit given to her for raising the issue at such an opportune time for me. I am going through a big closet purge right now, and I ran across three pair of shorts that I haven't worn for 2 or more years because they were uncomfortably snug. These particular items were for me both HEWIs and casual workhorses. But they haven't fit properly for a while so I told myself no more holding on - it is time to let them go. I applied exactly the same logic other have expressed here - that even if I were to drop a few pounds, my shape will likely be different, yadda, yadda, yadda.

Then for some strange reason, I decided to pull a pair from the discard pile and slip them on - And they fit PERFECTLY!!

But guess, what? The clouds did not suddenly clear from the sky. I heard no angels singing. I didn't even do a happy dance.

I thought: oh, nice - these will be useful in the next few weeks before the weather cools. Then I moved on with more closet purging.
Why was this not an epic moment? Because I think I have finally internalized a basic truth. If I had properly purged and reorganized my closet several months ago, in addition to ditching these re-discovered shorts, I would have gotten rid of another 6 bags of outdated items that have been taking up valuable space in my closet, and obscuring my ability to easily see and choose the pieces I really do enjoy wearing.

So when it comes to these decisions, for me at least, it is important to remember that the ultimate goal - to have a functional wardrobe - is what matters. This or that particular "lost opportunity" is irrelevant.

So, for those of you who are farther down this path, what is the next step? Once you knew what you DIDN'T want in your functional wardrobe, how did you identify - and find - what does belong in your ideal closet?