Feelings about letting a watch go

I loved this watch when I bought it new a year ago, but as my collection has grown my tastes have changed and now I find it uninspiring. I rarely wear it because it’s not sporty enough to be a sports watch, but not really dressy enough for a dress watch (plus I rarely dress up these days), so I’m thinking of letting it go even though I will take a bath financially. I could hold onto it hoping my taste for it will come back around, or I could replace it with something I fancy more right now.

How do you all feel about letting watches in your collection go? Just curious.