I'm hearing you on the 'Bought it! Love it! Don't love it enough! Out it goes!' cycle. It makes me distrust my judgement, and even if you can resell/consign something, there's often $$ lost, and definitely time and energy lost.
Maybe give yourself 2-3 weeks of NO buying (maybe even NO looking?) while you settle into fall (ha, you're in Austin!), okay while you ponder the internals of this and see if you gain any insights. (i.e. are you looking for new color, new silhouette, new proportions, ?)
No need to think of it as denying yourself forever, but pausing to give consideration to it all.
P.S. I don't know if you've jumped on the Equipment silk shirt bandwagon, but I can see you in one(in a color) worn loose over all sorts of your great bottoms.