Various embodiments provide for systems, methods, and computer-readable storage media for annotating a digital image with a texture fill. An annotation system may receive a user input defining a border separating a first portion of a target digital image from a second portion of the target digital image. The annotation system may then generate a contour mask, such as a binary mask, for the target digital image based on the user-defined border. The annotation system may then apply a media overlay to the target image based on the contour mask. In particular, the contour mask can define portions of the target digital image such that the annotation system will apply a media overlay to at least one of those portions while not applying the media overlay to remaining portions of the target digital image.