Novel pressure sensitive adhesives (PSAs) were developed from renewable methyl oleate (MO) and fully evaluated for their peel strength, tack force and shear resistance. MO was epoxidized and selectively hydrolyzed on the ester group to form epoxidized oleic acid (EOA) that is a bifunctional monomer containing both a carboxylic acid group and an epoxy group. EOA was step-growth polymerized to form a hydroxyl-containing polyester, which was then cured in the presence of a small amount of a polyfunctional epoxide [epoxidized soybean oil or trimethylolpropane triglycidyl ether (TMPTGE)] to afford PSAs. The PSAs from the polyester cured with TMPTGE exhibited high peel strength (2.4 N/10 mm), high tack force (5.8 N), and sufficient shear resistance (9.0 min). The PSAs can be fully based on renewable natural materials, and their preparations are environmentally friendly. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014, 131, 41143.