Star has some great advice. I would like a smaller wardrobe so closets are less crowded and things get more wear, less “ too many choices”. I am a very slow closet editor ( think agonizingly slow!) but make use of “ aha!” moments when I finally recognize what is “ wrong” with items I’m not wearing.
Aside from obvious signs of wear/ damage, easiest things are fit—really detailed fit which includes elements of silhouette and details like necklines , armholes, plus pinching, binding, riding up.
Next is color, as my coloring has changed over time.
“ Imaginary lifestyle “ is hard for me because I don’t really have anything too crazy or unwearable , but may have a higher % of this or that category. Sometimes duplicates when one would do, more outfit possibilities for a certain “ level” of wear when fewer choices would be better.
I get style inspiration and wardrobe editing inspo from various sources— sometimes just a tiny twist in that way someone says something give an “ aha” for me. Or the same words in a different season make sense.
Angie has some wardrobe revision or refresh posts. Allison Bornstein has her “ system”. Alyssa Beltempo also & has a lot of SYC/outfit creation videos to help inspire using your favorite pieces.
It does make some sense to start with a small group of things you KNOW you wear, & then expand. Or nibble from both sides— definitely yes and some definite No and then the vast middle ground.
I have room for a Holding Zone ( underbed boxes, so not ideal) and that helps me, or I’d get stuck. I have 2 types actually- a very small amount of “ teeny bit too tight” items, mostly a favorite pant/ Jean or skirt; and few things I think are no longer right but am hesitant. I have done pretty well making decisions about these in next 6-12 months.
If you have a very strong sense of your style it’s easier. Select or wear your very best outfits ( quality or just “ looks” and wear those, then do tryons of other things and compare. Some things will be “ close” and you may need to keep those in order to get dressed, but may plan upgrades, but the farther away things are from the bar you set, the easier to cull. My wardrobe got somewhat overload Ed due to retirement/ pandemic, and after, which seems paradoxical ( should need fewer clothes and I did cull much professional clothing), but I believe it had been the “ now what” after years of daily professional outfits, so trying different things, then too much super-casual, and so on.
Good luck! If you can find both your “ wardrobe style bar” to aim for, and your closet editing style, as to what approach works for you, that will help.