These waterproof Dansko boots are on sale and have worked for my clients who have fussy feet. They are comfortable, versatile, and quite supportive. You can remove the footbeds to insert orthotics, or add a cushioning insole for extra comfort. They work well for higher arches, but might be snug for high insteps. The heel is less than two inches, and the leather is soft.
They come in two colours. The dark brown version you see below is an inaccurate reflection of the colour. They look more like the taupe you see in the other pictures. The boots can work well with midaxi skirts and dresses, shorts, cropped pants or jeans, and full length pants and jeans. A reliable causally classic style.