This chapter traces the media representation of menswear for women and the stars who popularized it. One of the primary sites of struggle over gender roles in the 1930s was the workplace, and working women figured significantly in Hollywood films. These characters enact a range of tensions around women's social and economic autonomy. Such tensions can be seen in the decade's contrast between the adoption of menswear by women and a simultaneous revival of neo-Victorian, feminine styles. Costume played a significant role in Hollywood's negotiation of the contradictory roles that working women played in the 1930s. Casual menswear clearly signified glamorous androgyny, but tailored, professional clothing was often associated in films and magazines with the need to guard against sexual harassment in the workplace.