Personal stylists often mention a “capsule wardrobe” item. That is, those pieces in your closet that you can count on to look great, feel great and work as a base for the other items in your closet to facilitate easy dressing.
I too, recommend knowing which pieces in your closet are your strongest. Sometimes you gain or lose weight, have surgery that changes your shape, or the molecules of your body just rearrange themselves so what once looked good, does no longer.
For me, the button down short sleeve popover shirt was a go-to. I owned it in black, white and blue, and in silk and cotton. But, in recent months when I put one on, it just looked wrong. I can’t explain if it was the sleeve, my body, or that my eye just didn’t see it the same. I kept trying to make it work. I never actually walked out of the house with it on. I spent more time putting it on, and taking it off, then actually wearing one. So, if you keep trying to wear a piece of clothing you used to love and wear all the time, but now it never makes it out of the closet/bedroom/house, you too, may consider that it’s time to break up.