Transgender consumers struggle to have their gender identity recognized, resorting to clothing as a practical way to forge their identity. Intimate apparel represents the innermost type of clothing, carrying both functional and aesthetic roles for transgender individuals. When navigating the intimate apparel marketplace, transgender consumers are faced with vulnerability as their gender identity is stigmatized by society, negatively impacting their well‐being. This research focuses on understanding the neglected aspects of intimate apparel consumption by transgender consumers, discussing the role of stigma as it generates vulnerability in the intimate apparel marketplace. To gain insight into the multifaceted transgender people's intimate apparel consumption context, we conducted in‐depth interviews with 18 Brazilian transgender consumers. Data were analyzed using dialogical thematic analysis with a hybrid approach of deductive and inductive coding. Our findings revealed that: (1) the consumption of intimate apparel by transgender individuals involves a striking duality of both positive and negative aspects; (2) although transgender consumers see intimate apparel as a legitimate way of expressing their gender identity that carries symbolic meaning, functional aspects (e.g., comfort and fit) are also essential to them; and (3) intimate apparel plays a unique role during transgender people's social transition as they can choose whether to use those pieces privately or publicly, unlike most fashion products. Our key takeaway from this research is that consuming intimate apparel carries multifaceted meanings for transgender consumers, impacting their emotional and social well‐being in several ways.