The present study is theoretically located in the field of critical feminist studies of the representation of women in the mass media. It discusses the ways in which working women characters construct and express their occupational identity in selected American primetime TV dramas of the early 21st century. The observed strategies, which range from highly restricted self-expression to unbridled sartorial liberty, appear to be heavily correlated with the prestige of the presented occupations and their levels of masculinization/feminization. Moreover, the self-limiting sartorial choices of high-achieving professional women, frequently containing their femininity, result from the competitive nature of prestigious yet traditionally male-gendered occupations. However, it is also pointed out that working women are generally depicted as determined to accentuate the physical aspects of their femininity regardless of the established dress code or traditional gendering of their occupations. Thus, the sartorial choices made by the female characters at the workplace serve in the analyzed TV shows as symbolic manifestations of women’s growing confidence as players on the job market in their own right.