The supramolecular polymerization of diketopyrrolopyrrole (DPP) derivatives has emerged as a promising strategy for advancing electronic and photonic materials. Gaining a comprehensive understanding of how the structural design of DPP monomers influences their supramolecular polymerization behavior is crucial for the rational design of materials with tailored properties. In this study, a series of DPP derivatives sharing a common molecular framework but differing in core structures, terminal groups, and spacers is synthesized and investigated. The comparative analysis reveals that these structural variations significantly impact the kinetics and mechanisms of the supramolecular polymerization, as well as the aggregate morphologies of the resulting supramolecular polymers. These findings offer valuable information for the strategic design and precise assembly of dye-based supramolecular polymers with complex architectures.