1 and 3 (floral dress and blouse) don't look like they fit the style of "bold, breezy, elegant." I don't consider these soft, tiny floral prints to be bold and vote donate for that reason.
The shorts in 2, I wouldn't get rid of until you have a replacement since they fill a specific need.
The skirt in 4, I like a lot for the current aspirational style, it definitely says bold yet elegant to me. But, if it's showing signs of wear I'd start looking for a replacement.
The boho blouse in vibe, your label gives away, this is boho not elegant. I'd vote donate because it's not in line with your current style.
Sandals, these look elegant to me. If they are comfortable I vote keep, comfortable shoes are always hard to find and you may reach for them over time again since they were a previous workhorse. But only keep if you have room to store a shoe that may go unworn for a season.
Black floral two piece, this is actually my favorite of this group, it says elegant and bold to me, so I vote keep.