Soft wearables include clothing and textile-based accessories that incorporate smart textiles and soft electronic interfaces to enable responsive and interactive experiences. When designed well, soft wearables leverage the cultural, sociological and material qualities of textiles, fashion and dress; diverse capabilities and meanings of the body; as well as the qualities and capabilities afforded by smart and programmable elements. Textiles behave in particular ways. They are part of culture. No matter a person’s views on fashion, dress, their own or others’ body, they will have an intimate relationship with textiles, as they are one of the few products worn much of the time, often in direct contact with the body. When designing wearables a designer must consider a range of requirements that do not typically demand focus when designing products that are not worn, including: sensitivity to material detail; an eye for fit and comfort on bodies with diverse shapes and movement capabilities; openness to a diversity of meanings that may be generated; as well as consideration of wearers’ intimate relations with technology. Soft wearables allow for greater scope within these requirements. In this article, we discuss the opportunities and challenges of designing soft wearables, applying notions of situatedness and personal meaning-making to understand and posit values in relation to outcomes. We present three design cases that focus on body, material, and context; and reflect on how the different approaches impact use. Finally, we reflect on how embodied and collocated interactions might extend understanding of how to frame wearables research and development to arrive at rich interactions that are soft, embodied, situated and connected.