I think I struggle with the concept of *Essentials* because, I'm embarrassed to say, my wardrobe has grown so large that I could miss quite a few items and still get dressed.
My wardrobe is mostly gray (charcoal/mid-tone/marled/silver) and I pattern mix so swapping out one thing for another is no big deal. (I own most of what is in my Finds.) If I were to think in terms of what I would always want to have:
Sparkly/silver footwear
Combat boots because I need lace-up; not overly masculine
Oxfords because I need lace-up; not overly masculine
Dansko clogs(?) not sure; not as comfy as they used to be
Non-fishnet fishnets, as in open patterned weave. Bare legs are never warm enough, so fishnets work when tights are too warm.
Variety of watches because I wear a watch every day.
Coatigan because my house is cold and I get cold. I need sleeves wide enough to accommodate several layers underneath.
Shirtdresses that will allow jeans to be worn underneath. Easier to wear than a shirt with jeans and can also be worn as just a dress.
Patterned jeans (in gray etc.)
Sweater dresses (in gray/black/etc.)
Black work pants
Turtlenecks/funnel necks/mock turtles: Not a particularly flattering look on me, but a collarless neckline with a scarf just isn't warm enough for me. I don't like longer hair on me, so turtles it will be.
I feel like I should add white shirts because I seem to have accumulated so many of them. But I don't wear them that often, but I can't identify why. Maybe it's the temperature window during which I can wear them?