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@LeaVerou mentioned an element-shape property in #6980 (comment) as a way to influence the shape of an element. The idea behind that property is to change the shape of the element so that border, shadows, etc. follow that shape.
So far we have the shape-outside property which influences the float area. I suggest to extend this property to be able to specify that it not only affects the float area but also all the other boxes created for the element.