Born in Newport, Kentucky, Winstel is a graduate of St. Thomas High School in Fort Thomas, Kentucky. She received her BA in physical education and history from Northern Kentucky University in 1977. She was a walk in on NKU's first women's basketball team. She then after received her master's degree in physical education with an emphasis on coaching from Indiana University in 1978, then soon became head women's basketball coach at Midway College in Kentucky for three years. In 1981, she returned to NKU as assistant coach for the women's basketball and volleyball teams and head coach of the women's softball team for two years before becoming head women's basketball coach in 1983.