I think Angie and Adelfa are honing in on an interesting issue and i am going to try to keep that in mind. Uncertainty can mean time for a shift.
I recently tossed a number of things just going more by my instincts than an intensive analysis, and the fact that if I had questions about something, there was likely to be something better eventually and more likely to happen if I let it go.
It's maybe a little harder with semi-special occasion wear --some shoes and dresses, for me--because I have to be careful not to toss the only thing I have for a certain event just because it's not in regular rotation, or not a "10" , or at least to decide whether to add a wardrobe hole to the list.