Short answer
Stability first. Then fit. Height is the last variable.
An eight-hour day tests a shoe differently than an evening out. The heel needs to hold steady across surfaces — office floors, pavement, stairs. That requires a base wide enough to stabilise the ankle without visible bulk.
Secure hold at the upper matters as much as the sole. A foot that slides forward inside the shoe creates forefoot overload regardless of heel design. The fit should lock the foot into position so the structure does the work.
Moderate pitch with a leather sole and no synthetic lining reduces heat and friction. The shoe should feel firm at first and settle within the first hour — not the other way around.
This is not medical advice. Consult a specialist for persistent discomfort.