Individuals with atypical breast shape/size often find it quite challenging to obtain a comfortable, supportive, and fitted bra off-the-shelf. They include people with very large breasts, who have significant breast asymmetry, and/or have undergone mastectomy or mammoplasty. This paper provides insights in their challenges and attempts to fill the gap in terms of critical review of the current state of knowledge around the topic of bras. Poor and ill fitted bras are associated with breast, chest and shoulder pain, embarrassment, and an overall reduction in quality of life among others. Building upon the advantages and limitations of solutions to improve the fit, support and comfort of bras found in the literature, this paper proposes strategies to solve these challenges. As the problem is multidisciplinary, a human-centered interdisciplinary approach is key to ensure that all aspects are considered at all stages of the process. A modular design allows selecting the fabric characteristics based on the requirements of each bra part. In terms of materials, stretch woven fabrics offer a large potential in the production of bras to enhance the support provided by areas such as the under band and back panels. Bespoke manufacturing takes into account the specificities of each individual. The road map proposed here will contribute to enhance the quality of life of individuals with atypical breast shape/size.