Arrange the sugar cookies on a clean work surface so each one has room for decorating.
Spread a thin layer of chocolate frosting across the top of every cookie using a small spatula or the back of a spoon.
Dip the frosted side of each cookie into the black sanding sugar to coat the surface evenly.
Add a small dot of chocolate frosting to the center of each cookie.
Press one milk chocolate kiss onto the dot of frosting on every cookie to form the hat shape.
Scatter orange sprinkles around the base of each kiss for added color.