While the number of women entering medical schools is approaching 50% nationally, women continue to be underrepresented in a number of specialties including diagnostic radiology. While diagnostic radiology has many characteristics that might be desirable to women, such as reasonable call hours, flexible scheduling, and high salaries, women still do not choose diagnostic radiology as a career. This article examines the literature to discern possible reasons for why women are entering diagnostic radiology at a lower rate. We address trends among women in academic medicine, which resemble trends among women in diagnostic radiology, and examine the effects of gender and socialization in medical school on specialty choices among women. The current literature suggests a constellation of factors may be responsible for the gender differences in diagnostic radiology. We suggest that further research is needed to elucidate why women do not seem to be choosing diagnostic radiology as frequently as one might predict based on the lifestyle of diagnostic radiologists and the numbers of women currently entering medical school. Once these reasons are made clear, it will be possible for residency program directors and medical schools to ensure that women are making informed specialty choices, whatever those choices may be.