This study demonstrates the self-assembly of N- and C-terminal protected dipeptides Phe–Gly and Pro–Gly which were derived from amyloidogenic and elastomeric peptide sequences. These constituents afforded nanostructured supramolecular ensembles through various non-covalent interactions in the solid state which can be directly correlated with their fibrillation event in solution phase. Interestingly microscopic observations revealed that the amyloidogenic dipeptide constituents assembled into hollow tubular structures whereas the elastomeric dipeptide constituents assembled into the feather or sheet like structures.