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I recently did something similar to this, since over the past 12 months my dress size has altered somewhat, and doesn't appear to be changing back. I waited a while, just in case, then decided to sell them on. I used the cash from the sales to replace my wardrobe - although I am still deeply upset that some of those items couldn't be replaced.
Ultimately I chose to perceive it as a sort of renewal, a closet cleansing. It was doing me no good to mope!
Although my own circumstances were born of necessity, there is also something quite exhilarating about being faced with the prospect of renewing an entire wardrobe (slowly, admittedly, as my finances allow).
On the other hand, I do so wish that I had the means to store everything that I have ever owned over the years. So many items that I parted with many years ago for various reasons might delight me today, so I always try to think ahead if contemplating a de-stash. I will probably also regret the garments that I have recently sold to make way for new, better fitting items, simply because at some point I imagine that something, just something could have been altered, reworn in a new way.....etc, etc.
I agree that it ought to happen gradually in most instances, though. Such wise words!
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