Current fashion research has not explored women’s perceptions of available clothing choices during the biological and physical transformations of midlife. Instabilities such as menopause, family breakups, or a loved one’s death augment women’s diminishing visual presence amid Western society’s beauty ideal. In response, clothing may become vital for self-expression, but also measurable in the terms of dress success, or a wardrobe impasse. A reflective Photovoice approach required participants (n=11) to take 7 full-body selfies over the course of a week, while wearing their favourite daywear outfits. The photographs prompted in-depth discussions during one-on-one interviews. Photovoice’s debut in fashion research reveals the common philosophies and strategies used by women in midlife to navigate a quick-response fashion system and establish a wardrobe that reflects their self-image. Women’s personal perspectives and selfevaluated dressing choices reveal whether their everyday wardrobe supports or compromises their desired self-image, promoting dress success or causing a wardrobe impasse.