Commercial sex has been a complex and controversial issue in Taiwan. It was banned several times and finally partially legalized in law when the Congress finally amended Article 80 of the Social Order Maintenance Law and authorized local governments to establish red-light districts. Unfortunately, in reality, until now, no local government has established a red-light district. Therefore, all commercial sex is still illegal in Taiwan. By reviewing this issue from gender, culture, and legal perspectives, this paper discusses the regulation of commercial sex in Taiwan in three parts. In the first part, this paper provides a historical view of the development of commercial sex and how the government regulated it in different periods. In the second part, this paper introduces the debate and various perspectives of feminist legal theories on this issue. Finally, compared with the regulation models of Japan and Singapore, this paper proposes an empowerment approach in response to the current Social Order Maintenance Law. Focusing on sex workers’ autonomy and subjectivity, the new approach hopes to balance the interests between the rights of sex workers and the needs of social order and public health.