The invention of the commercial sports bra in 1977 was a significant advancement for physically active women. Despite its humble origins as an enabling technology, the sports bra has since been invested with new and varied cultural meanings and currencies. In this article I critically read popular representations of sports bras, specifically advertisements and “iconic sports-bra moments” that circulate around Brandi Chastain’s celebration of the U.S. women’s soccer team’s victory in the 1999 World Cup. I argue that such representations sexualize sports bras and the women who wear them. In addition, these representations homogenize and normalize ideals of femininity, which are considered achievable through technologies of disciplined body management, and reproduce the traditional gender order.