Linnae Way is a very comfortable heeled shoe by Clarks. Premium leather uppers are lined with a combination of leather and textile, creating a very natural and breathable feel around the foot. The ~1.75" heel is easy to wear thanks in large part to a removable footbed which provides both cushion and some support. Twin elastics help get them on, and the extra foot coverage helps keep them on.

Available at Glebe Trotters.