This dissertation considers how district-level demographic factors favorable to women congressional candidates facilitate substantive representation of women's interests. I contribute to the existing research by linking the literature on women candidate emergence and electoral success with that on descriptive and substantive representation. Beyond simply asking whether and how women in Congress represent women's interests, I argue that the demographic characteristics of districts in which women are more likely to run and win public office also put women representing those districts in Congress in better position to cultivate feminist homestyles and substantively represent women's interests through legislative behavior. I examine whether women representatives in women-friendly districts are more likely than men representing similar districts, or women in less women-friendly districts, to sponsor legislation in women's issue areas, sponsors women's issue earmarks, and defect from party in women's issue roll-call votes. Overall, I find general support for my theory that district-level factors contribute to observed gender differences in legislative behavior in women's issue areas.