Yes sometimes that happens.
I added some check culottes last year that I really like. But they really only suit May-September. I have worn them four times this year and I think I wore them 6-7 times last year. They are quite a statement and not that versatile. I suspect they will never get to 30 wears to be honest.
But they were locally made by my friend, inexpensive ($60) and I get joy from wearing them. So a few pluses!! It is when something fails, or is an expensive mistake that I feel more disappointed.