My wardrobe has always been essentials heavy. I find them the easiest items to buy and to identify. It interests me that so many people have trouble with this concept and I wonder why. I suspect it comes more easily for those with a style that leans heavily classic? It might be more difficult if you are an eclectic dresser.
Anyway, here is my list for 2019 in the hope it might help someone else. One way I think of this is -- it is a very rare outfit that does not include at least one of these elements. The ones I pull into play most frequently vary with the seasons --- the white sneakers are a summer essential; the navy booties, a winter essential, and so on. But if you look back over your WIWs, which items or elements get repeated again and again in different outfit combinations? Which items do you miss when they are in the laundry? Which do you reach for in those "ugh! What shall I wear??" moments? That should offer clues.
1. Navy crewneck or turtleneck knitwear (for different seasons). (High five, Angie!)
2. Blue and white striped knitwear, or white and blue (for various seasons). (Ditto!)
3. Navy blazer
4. Slim high waisted jeans in blue and in white. (I have and enjoy other jeans but these are the essentials).
5. Long grey cardigan.
6. Denim jackets (esp. in summer — not really in winter at all.)
7. Classic navy blue outerwear. (High five, again, Angie!!) Oh, and I desperately want a military coat like yours. On my list of HEWIs. As well as an upgrade of the consignment pea coat, which is working really well for now but is not "the one."
8. Silver or soft grey footwear across all seasons. Must have a dressy bootie, a casual bootie, a sneaker, a sandal.
9. White footwear (summer); navy or ink footwear (winter).
10. Silver watch and earrings. Belt with silver hardware.