It’s a lovely dress, but it feels like it belongs down a different path than the one you’re taking. The ornate pattern, body-con cut, and classic vibe aren’t what I associate with your current style. And it sounds like most of the items you’re on the fence about would be easy to sell or consign, or would be appreciated by Dress for Success or a similar organization.
I don’t think of myself as a ruthless editor, but I cull roughly three dozen items each year (I don’t set a quota, but that seems to be my typical
in/out number), mostly due to wear and tear but sometimes because my tastes have moved on. Something going unworn for more than a year is a good sign I ought to re-home it, unless it has a very specific purpose (like a pair of black oxfords for job interviews and funerals).
Once I start asking if a piece ought to go, it usually means the answer is yes. I can think of a few things I wish I’d held onto; I culled a lot more when I was younger, moving frequently, and had little storage space. But in the end, it’s not the end of the world and better to feel I have “enough” than “too much”. I don’t want to collect clothing; I just want to enjoy wearing it.