Poly(2-oxazoline)s are an interesting class of synthetic poly(amide)s that can be prepared by living cationic ring-opening polymerization. The properties of poly(2-oxazoline)s can be tuned by variation of the 2-substituent of the 2-oxazoline monomer. In this contribution the utilization of fatty acids as side chains for poly(2-oxazoline)s is highlighted. The incorporation of such long aliphatic side-chains results in hydrophobic crystalline poly(2-oxazoline)s that are often applied for the preparation of amphiphilic structures as well as for low surface energy and low adhesive coatings. The most popular fatty-acid based poly(2-oxazoline)s are the saturated poly(2-nonyl-2-oxazoline) and poly(2-undecyl-2-oxazoline) as well as the unsaturated poly(2-decenyl-2-oxazoline) and poly(2-“soy alkyl”-2-oxazoline).