Short answer
One prioritises the line. The other prioritises the stance.
A stiletto narrows the contact point to a few square centimetres. Visually sharp. Mechanically demanding. The ankle works constantly to stabilise what the base cannot, and on uneven ground — cobblestone, gratings, grass — the margin for error disappears.
A structured heel widens the base without adding visual weight. The ankle loads less. The gait stays controlled. The trade-off is a different silhouette — less knife-edge, more architectural.
Neither is objectively better. A stiletto is the right choice for two hours at a table. A structured heel is the right choice for six hours on your feet. The question is not which is more elegant — it is what the day requires.
This is not medical advice. Consult a specialist for persistent discomfort.