I am continuing to make some progress in editing wardrobe to get rid of fluff and meh and duplicates.
Did a post on, when hitting some kind of dither-wall on an item that I like but have not been wearing, I would do some try-on's to see whether there was even one great outfit that an item could be used for, as a minimum standard, though might not be enough.
One thing that sometimes helps is what I call the "jeans test."
First, you have to put on some jeans! For me it should be my most flattering pair, or for those with extensive denim collections, might need to try with some different styles.
I have found that if a top or jacket does not work with a pair of good-fitting, darkwash jeans, it may be hopeless. The test can work with loafers and flats, too.
My basis is that the jeans, while potentially classic, are often my most "modern", youthful (not "young") item and due to the magical properties of denim, overcome some pants-fit issues. And they tolerate a range of fits in the other items , such as, tailored, boyfriend, long, short-over-a longer-tank/T, oversized, but can disclose whether that fit is intentional (such as "BF" fit vs too big or baggy).
The test breaks down for some items and fits which are intended for high-waist or high-volume bottoms and certain proportions, but can be a really good reference point.
It is basically just a variation on seeing if an item can be re-mixed/re-invigorated if worn with something that carries its own weight in style, updated-ness, and happiness-factor. Plus the denim works as a neutral, so the item's color has to stand for itself.
I think it works for me because I don't wear jeans every day and because there are fewer rules for denim (can go dressy, casual, untucked, sparkly--a whole range).