An absorption and circular dichroism spectroscopies investigation was carried out on the heteroaggregates formed in water upon the interaction of Chicago Sky Blue with four different cationic surfactants derived from ephedrine and pseudoephedrine and featuring hydrophobic tails of different length. The chirooptical features of the heteroaggregates indicate that hydrophobic interactions control the transcription of the chiral information from the surfactant to the supramolecular architectures they form with the dye. In fact, surfactants characterised by the same stereochemistry and by different length of the hydrophobic tails mediate the selection of the enantiomers of the same chiral topological arrangement.