Love that combination!
Happens once in awhile.
I think the item has to have some element of perfect fit and usually flattery. So that you just like how you look in it, so one day it might all come together.
I find that a useful concept when doing wardrobe review of "holdiing zone".
Sometimes the item was great in my last memory of it, but now the fit is off. Not just talking the fluid vs oversized thing, but, really doesn't fit. Then I can tell it needs to go.
For example, I had a long black A-line skirt for formal occasions and had not worn it in years. But, tended to think it was "classic" and waiting for a top. This fall I tried it on and it was actually too big in some areas, but also it just no longer looked like anything I would want to create an outfit around. So, pouf, out it went.
But the keepers have something about them such that you could say, if this were featured in stores now I'd want to buy it.
The most common items like this for me are skirts and dresses, since I don't have as much of a skirt and dress life both due to lifestyle and to footwear, and a few wide-legged pants. If the fit remains really good I'll keep it and consider it might get a new life. Of course it may be that only a "new version' will do, so they may get tossed after awhile.
Also footwear as Angie said. Again, have to try on at least once a year to see if it is what it was.