A simple and efficient strategy to modulate the self-assembly and solid-state morphology of conjugated polymers has been developed by incorporating various amounts of amide-containing alkyl side chains to high charge carrier mobility conjugated polymers based on diketopyrrolopyrrole (DPP). Synthetically easily accessible and tunable, the incorporation of amide-containing side chains is a direct strategy to promote intermolecular hydrogen bonding between polymer chains and tune the solid-state morphology. Incorporation of 5–30 mol % of amides in the conjugated polymers was performed without a drastic decrease of solubility. The incorporation of hydrogen-bonding moieties allowed for an improvement of the charge carrier mobility in organic field-effect transistors (OFET) devices, which achieved a maximum value of 2.46 cm²/(V s) at 5 mol % of amides. Morphological investigation showed that the intermolecular hydrogen bonds formed between adjacent amide moieties directly affected the lamellar packing of the polymer and aggregation, without affecting the π-conjugation. Therefore, controlled self-assembly of conjugated polymers through hydrogen-bonding side chains is a promising strategy toward more efficient semiconducting polymers for thin film transistors and other organic electronics.