The encapsulation of vegetable oils within an aqueous dispersion of polymer nanoparticles provides an alternative route to create functional paper coatings from renewable resources, by combining the presentation of hydrophobic moieties together with variations in roughness at the paper surface. The effects of two selected vegetable oil types, i.e., castor oil and hydrogenated castor oil (wax), are compared in terms of nanoparticle synthesis, coating hydrophobicity and surface gloss. The nanoparticles were synthesized by adding 50 wt.-% oil during imidization of poly(styrene-co-maleic anhydride) with ammonium hydroxide. From evaluation of the thermal properties, the nanoparticles have a high glass transition temperature that is suppressed in presence of oil. The nanoparticles with hydrogenated castor oil have higher imide content and better thermal stability compared to castor oil, in parallel with lower chemical reactivity of the hydrogenated oil and less interference with the imidization reaction. After deposition as a coating on paper, the physical coating properties are discussed in parallel with the coating chemistry and morphology or roughness at different scale lengths. The nanoparticle coatings with hydrogenated oil provides a multi-scale roughness with an open, porous nanoparticles structures and presentation of some amount free oil augmenting hydrophobicity towards a water contact angle of 128° (static contact angle) or 138° (advancing contact angle). The differences in surface coverage of coated papers in terms of imide and oil contents are confirmed by chemical Raman mapping. The differences in surface roughness are confirmed by non-contact profilometry, laser interferometry and atomic force microscopy.