Refined olive oil (ROO) was blended with tristearin (TS) and palm oil (PO) at two different ratios (ROO:TS:PO; 75:15:10 and 85:10:5) and chemical interesterification was performed in order to produce two interesterified fats (IF1 and IF2) with high unsaturated fatty acids and low trans fatty acids contents. Solid fat content (SFC), slip melting point (SMP), and fatty acid composition were determined in IF1 and IF2; the values were compared to that of partially hydrogenated industrial cookie shortening (ICS). Higher SMP was measured in interesterified fats contaning 75% ROO (IF1) and lower SMP was obtained in interesterified fats containing 85% ROO (IF2). SFC values of interesterified ROO blended oils were lower than ICS. Interesterified fats were used for cookie production, and cookie quality parameters, including oxidation stability, were determined. Results showed that hardness values of cookies were not affected by fat types and higher spread ratios and lighter colors were obtained. IF1 and IF2 had higher total oxidation values as compared to ICS.