I'm trying to have a more intentional, curated wardrobe but at the same time finding unexpected new style directions occasionally.

Also, I find that sometimes my list just isn't happening, and a wardrobe hole, or something I intend always to have on hand as a good "essential, " isn't turning up.

The concept I have in mind isn't quite the same "settling" for something that isn't good, but more on the order of, if you find something that seems off the path but looks really good on you (again, that would be hoping we've judged it accurately) , should I get it and build some outfits around it and allow wardrobe direction to shift--as a happy serendipity.

I guess part of the answer to my own question would be, can I wear it with several other things or does it require majoroso new purchases; is it for the imaginary lifestyle or does it help you expand your lifestyle or "live with more fashion gusto"--that sort of thing. Sticking within the wardrobe color pallette helps reduce the chance of something being a big mistake, I think, but not always (as in, skip the tendency to buy something just because it's MY color.)

Part of this idea comes from the fact that certain items seem absent some years or seasons. My made-up scenario is this: perhaps one is a black blazer person but your black blazer died and you just haven't found a good enough replacement. So instead you embrace the black cardigan, or you happen to find a red blazer that's fab and you become a red blazer person for the next year or so even if it requires a few extra purchases, or maybe you find a funky edgy jacket and just say, heck with black blazers.

Or, maybe this type of thinking is just settling, and that's the drugs talkin'.

I do think chucking out stuff that's not fab and letting wardrobe gaps develop is healthy for progress (for me, that is) through either planned PPP or serendipity, because I never realized before how the "emptiness" would make it more likely that something better would happen, whereas, if I keep stuff I'm not wearing, I neither wear nor move on.

How about you--do you have a kind of yardstick for when an item or outfit shift is where you're meant to go, vs. getting you off track, or related experiences to share ?