Ionic liquids (ILs) have attracted increasing interest in science and technology because of their remarkable properties, which can be tuned via varying ion structures to control the relative strengths of Coulomb interactions, hydrogen bonding (H-bonding), and dispersion forces. Here we use atomic force microscopy to probe the interfacial nanostructures of hydroxy functionalized ILs at negatively charged mica surfaces. H-bonding between hydroxy functionalized cations (c-c) produces cation clusters and a stronger interfacial nanostructure. H-bond stabilized cation clusters form despite opposing electrostatic repulsions between charge groups, cation-anion (c-a) electrostatic attractions, and (c-a) H-bonds. Comparison of ILs with and without OH functionalized cations shows directional H-bonding enhances interfacial structure more strongly than the dispersion forces between alkyl groups. These findings reveal a new means of controlling IL interfacial nanostructure via H-bonding between like-charged ions, which impact diverse areas including electrochemical charge storage (batteries and catalysis), electrodeposition, lubrication, etc.