Phytoestrogens are hormonally active compounds present in plant foods that are being studied extensively for their potential roles in hormonally-sensitive neoplasms such as prostate cancer. We postulate that the evidence for a protective role of phytoestrogens is not conclusive enough for a general recommendation for their use as dietary supplements, but phytoestrogens can be considered for therapeutic use in prostate cancer patients under certain circumstances. A literature review was performed to study the evidence regarding the chemopreventive role of phytoestrogens in healthy men, the protective role in early prostate cancer, and a possible therapeutic role in advanced prostate cancer patients. Dietary supplementation with phytoestrogens for chemoprevention of prostate cancer is still a debatable subject. Numerous pre-clinical in vitro studies have been promising, and novel molecular mechanisms of action for phytoestrogens continue to be identified. However, human clinical trials including studies done on prostate biomarkers and on the effects of phytoestrogens on steroid hormones are complicated by the possibility of local paracrine effects in prostatic tissue by phytoestrogens that are steroid-like in structure. Their interaction with multiple enzymes represents a paradigm for the complexity of phytoestrogen effects and a window into a potential reason that study results are inconsistent or difficult to explain. A final outcome of the phytoestrogen effect in the intact human may be difficult to discern because these agents can inhibit or induce enzymes, destroy cancer cells, yet will have intrinsic estrogenic effects themselves. Larger multi-center, multi-national, randomized controlled trials are needed before definitive recommendations can be made on the usefulness of phytoestrogens for chemoprevention and therapy for prostate cancer. However, combinations of phytoestrogens with radiation therapy and other antioxidants in advanced or metastatic prostate cancer can be considered because there are limited effective therapy options for this group of patients.