greenglove, this is a fun but challenging dilemma to have, after participating in YLF for a few years.
When to hold 'em, and when to fold 'em. (Not referencing Marie Kondo!)
I have 2 goals, that hopefully can be aligned--want to have fun being reasonably "current" but don't want to churn through entire sections of wardrobe frequently. It's okay to turn over some items each season or year that I've had fun with and moved on, but a modest amount, or for me it becomes the opposite of having fun, since that's wardrobe maintenance, not wardrobe-wearing.
Have an unabashed skew toward flattering fits, with a toe in the water on JFE--usually for me there's a method combination, e.g., my experiment with culottes is because they are waist-defining/long-torso adjusting, but lengths are JFE (if that!).
So, maybe 70's flare-leg revival will increase the odds of finding more bootcut options that wearable, but I will not likely want the very dramatic versions.
I may end up with loafers and oxfords being my style+ comfort+ individual choice look, and I would hate for really good shoes to get only 1 year of wear, but at least I can look out for "trending" colors or details or spinoffs--I got some inexpensive monkstrap style shoes this year that have seen a lot of use.
Maybe more tailored fits will increase the odds that several types of fit look current, so items have a longer shelf life, or that it's hard to make a distinction, so you can go with your "best" fit.
Footwear is interesting to me to try to see it as all about how to package the basic "foot"--meaning, I need toe room with slimmer or adjustable fit through the rest of the foot, low heels or slightly higher blocky heels, and certain vamp or shaft styles to work with specific pants. Over that can be a variety of embellishments, color, materials, heel shapes, sometimes modest differences in toe shapes. "Think outside the toebox!"
