This article highlights chemical modifications like alkali treatment, dinitrophenylation, benzoylation, and benzoylation-acetylation carried out on an pineapple agrowaste leaf fiber (PALF). The parent and chemically modified PALF were characterized by FTIR spectra, pH measurement, and detection of nitrogen. The percent moisture regain (extent of hydrophobicity), mechanical strength, and chemical inertness of parent and chemically modified fibers were evaluated. The modified fibers showed significant hydrophobicity, improved mechanical strength, and moderate chemical resistance.