A series of sugar-appended Schiff base chiral rod-coil amphiphiles with various alkoxy chain lengths have been synthesized in order to elucidate the variation of the helical twisting power (HTP), that is, the inverse of the pitch length, of the helical texture in the self-assembly of the amphiphiles. The HTP induced by chiral sugar in the self-assembled helical morphology was dependent upon the alkoxy chain length. Increasing the alkoxy chain length caused the self-assembled morphology to change from platelet-like texture to helical-twist morphology with varying pitch length and then revert to the platelet-like texture. This result demonstrates that the HTP reaches a maximum as the alkoxy chain length changes. The transformation from platelet-like to helical-twist morphology is induced by significant steric hindrance, when the effective size of adjacent alkoxy chains reaches the threshold of helical twisting and bending, resulting in the formation of a chiral smectic C phase. However, as the alkoxy chain length increases further, the disordering of the alkoxy chain conformation in the smectic-like layered structure may give rise to a structural imperfection that reduces the steric-hindrance effect. Eventually, the steric-hindrance effect may reach a compromise with the structural imperfection to produce a platelet-like morphology, leading to the formation of a low-order smectic phase.