Great insight. I really love how we are all learning on this journey.

Debbie, more and more that is what seems to be the deal for me. First, right fit. Then, right top with right bottom or topper and so forth.

Take pants. Pants usually either fit or don't, even in various styles. I mean, pants are still very hard no matter what, for me, but some are good. So there's the tapered pant that really fits, the bootcut, the straight--for each one there's some element about the waist and rear and hip and so forth that says it's a keeper or not (with tailoring where possible).
At times I've been about to toss a pair of pants but then said, these fit as well as any I've found, so it's either a) haven't figured the right top--it needs to be longer, or curved hem, or not clingy, or something--or shoes--so hem falls, or re-hem for flats, or something, OR b) do I think I will never wear this style even with the right other items? Or do I want to think about what type of update would make them work.

Whereas, if the pants upon review are tight, or saggy, or crease or flare in wrong place, or too short and can't be let down, or something.

I'm not saying I am not buying new pants each year, but am learning to see if it's the pants' fault or it's an outfit styling problem.