The synthesis, aggregation, and optical properties of a chiral, regioregular, HT-coupled polythiophene, substituted with a conjugated substituent, are studied. The side-chain contributes to the absorption, emission, and redox behavior of the material. Since the consecutive side-chains are, due to the HT-coupling pattern, not in direct conjugation, their electronic properties resemble well those of the monomer and are independent of the conditions. It was also shown that the conjugated side-chain chirally stacks in conditions in which the polymer backbone aggregates but the monomer does not, which demonstrates the ability of conjugated polymers to induce a (chiral) lamellar organization of conjugated moieties, present in their side-chain. Finally, it was shown that the conjugated side-chain can selectively be oxidized, without oxidizing the polythiophene backbone.