This article focuses on the development of design strategies and self-assembly pathways of metal-based systems incorporating Schiff base ligands. Versatility in Schiff base ligand design provides the possibility of straightforward modulation of a variety of structural features that dictate the properties of corresponding molecular metal complexes and supramolecular assemblies. First, mononuclear metal complexes are characterized in general terms, which is followed by a description of their application as building blocks of functional macromolecular/supramolecular structures. The metal-directed self-assembly of Schiff bases has also experienced considerable attention in offering a route toward the fabrication of multinuclear assemblies. By using different rigid or semirigid Schiff base-based scaffolds, numerous types of metallacycles have been constructed, either through stepwise or one-step procedures; triangles, square, and rectangular boxes, cages, and hexagon rings are some of the assemblies that have resulted from these approaches. Macrocyclic assemblies based on Schiff bases were shown to generate various types of mechanically interlocked molecular architectures, such as catenanes, Borromean rings, and knots. Additional structural and functional properties have also been created using Schiff base-based metalloligands, which offer structural rigidity and additional functional groups to a preorganized conformation. This type of metalloligand is particularly prone to be further involved in the assembly of coordination polymers of various dimensionalities and functionalities.