Merging closet purging guilt and bootcut/flare themes here, to achieve some sort of alchemy......

Let's say you had a pair of bootcut pants that still fit and flattered excellently (that would be key) but they seemed "out of style" .
Would you:
a) toss them, and a year or so later buy another pair that would then be defined as Modern Classic just because you bought them in the current calendar year?
b) Save them in the hold bin and only bring them out if they were trending again, (and then maybe find they don't fit, have a moth hole, etc)
c) Keep wearing them but work reallly hard (having fun doing so, of course!) to mitigate the un-trendiness with other updates you like anyway ( oversized sweater or high-low or cropped or whatever is your cup of tea, plus footwear.

I have yin-yang moments of really understanding updating items vs feeling a pawn of fashion winds and re-buying same things. And Ihink it might apply best to particular body type/item type items that continue to "work" and transcend other changes in styles--dressiing your particular body.
So I think I can usually identify when "my eye" may have changed for good on a particular item--if you look hard, there is something off about the fit, the "I wouldn't buy it again thing"

But in some of my save-the-planet or budget-conscious moments, I think I reallyl want to identify those items that I want to keep wearing (until it wears out, doesn't fit) but also want to really wear as part of a modern outfit and yet don't have the complete Personal Style confidence to do so without some work--but I think I'd feel rewarded and satisfied if I could.
This is where I could border on having or avoiding purging guilt, I think and can be over-influenced, even by YLF, by an overabundance of ttrend/update images and messages compared to what people are actually wearing in most of the country.
Sort of Update with a dose of Reality.