<p>In contrast to cyclic polymers with ring-like backbones, side-chain cyclization is another intriguing structural feature that has not been extensively studied. In this study, a library of orthogonally protected monomers featuring monocyclic, dicyclic, or tricyclic pendant motifs was designed and prepared based on malic acid derivatives. Polyesters with precise chemical structures and uniform chain lengths were prepared modularly through iterative growth. Meticulous control over the chemical details allows for a close investigation of the topological effects on the polymer properties. Compared to their linear side chain counterparts, the presence of cyclic pendant groups has a significant impact on chain conformation, leading to a reduction in hydrodynamic volume and an enhancement in the glass transition temperature. These results underscore the potential of tailoring polymer properties through rational engineering of side chain topology.</p>