This jacket is gorgeous on you, and the entire outfit is so rich and also playful.
Re the cropping -- hard to say for me because it depends on your weather. If you like them a lot and are into crops now, go for it.
I'm a fairly ruthless editor. Here's one reason. For years (I mean, since the 80s) I had kept some amazing Merimekko and Vuokko dresses. Oh, how I adored the fabrics and patterns, and I so wanted them to work again for me! The fit had never been great, though. They were samples and too large for me at first, and then too small in the hip as I gained weight over the years. Then I lost weight, and at that point they really were unworkable because they too voluminous.
I had them altered, but honestly, they weren't the same. They just didn't work. And one of the Vuokko's had moth-holes (sob!!).
So. All that is to say, I sometimes think taking a photo of the beloved item (perhaps with you wearing it) is a smarter idea than hanging onto it.
I've never really regretted letting anything go; I know that eventually I will find another beautiful item to fill the purpose if I need the purpose filled.
Yet I do see the point of saving certain things. I have a vintage Biba kimono, for instance, that I'll never let go. It may go in and out of vogue over the years, but such a great "third piece."
I think maybe hanging onto "third pieces" and statement items makes more sense?