Natural fur with a high density of soft hair fibers was selected as a model hairy surface to study the interaction of microalgae/zoospores with this biomimetic surface covered with “hairs”. The synergistic antifouling (AF)/fouling-release (FR) effect of the hair fibers and the surface chemical composition after grafting polymer brushes onto the hair fibers using surface-initiated atom transfer radical polymerization (SI-ATRP) was also explored. A series of laboratory static and dynamic settlement assays with microalgae and zoospores were carried out to systematically investigate the relationship between the modified poly-sulfopropyl methacrylate (PSPMA) brushes, the density/shape/length of the hair fibers and the AF/FR properties. The results indicate that the polymer brush-modified hairy surface can be effective against the settlement of microalgae/zoospores in different bioassays, especially in dynamic settlement assays. In general, hairy surfaces of higher hair fiber density, and with longer fibers, tend to display lower settlement of microalgae/zoospores, and the surface modification of the hair fibers with PSPMA brushes can strongly improve their AF/FR properties.