To automatically assess the aggressiveness of prostate cancer (PCa) lesions using zonal-specific image features extracted from diffusion weighted imaging (DWI) and T2W MRI. Region of interest was extracted from DWI (peripheral zone) and T2W MRI (transitional zone and anterior fibromuscular stroma) around the center of 112 PCa lesions from 99 patients. Image histogram and texture features, 38 in total, were used together with a k-nearest neighbor classifier to classify lesions into their respective prognostic Grade Group (GG) (proposed by the International Society of Urological Pathology 2014 consensus conference). A semi-exhaustive feature search was performed (1-6 features in each feature set) and validated using threefold stratified cross validation in a one-versus-rest classification setup. Classifying PCa lesions into GGs resulted in AUC of 0.87, 0.88, 0.96, 0.98, and 0.91 for GG1, GG2, GG1 + 2, GG3, and GG4 + 5 for the peripheral zone, respectively. The results for transitional zone and anterior fibromuscular stroma were AUC of 0.85, 0.89, 0.83, 0.94, and 0.86 for GG1, GG2, GG1 + 2, GG3, and GG4 + 5, respectively. This study showed promising results with reasonable AUC values for classification of all GG indicating that zonal-specific imaging features from DWI and T2W MRI can be used to differentiate between PCa lesions of various aggressiveness. © 2019 The Authors. Journal of Applied Clinical Medical Physics published by Wiley Periodicals, Inc. on behalf of American Association of Physicists in Medicine.