The family of ovarian sex cord–stromal tumors (SCSTs) includes a morphologically diverse array of benign and malignant neoplasms. Many of the benign SCSTs bear striking morphologic resemblance to malignancies in the SCST, epithelial, and germ cell tumor families. Chief among these are microcystic stromal tumor, sclerosing stromal tumor, cellular fibroma, typical thecoma, stromal luteoma, Leydig cell tumor, and pregnancy luteoma (a non-neoplastic hormonal proliferation). Although many of these entities are uncommon, awareness of their clinical, gross, and morphologic features is important to avoid overtreatment, particularly during intraoperative evaluation. Familiarity with newer immunohistochemical markers FOXL2 and SF-1 offers advantages over the traditional SCST markers calretinin and inhibin. This review addresses the distinction of benign sex cord stromal tumors from their malignant morphologic mimics.