The effects of oligomer length, solvent, and temperature on the self-association of stably folded short aromatic oligoamide are probed. With large flat surfaces, these aromatic oligoamides undergo stacking interaction with strength that increases nonlinearly with oligomer lengths. Opposite to typical aromatic stacking, the stacking of these molecules is enhanced in solvents of low polarity, but it is greatly weakened in polar solvents, especially those with hydrogen bond donors, and it is very sensitive to changes in temperature.