Perceptions of the boundaries of masculinity have often been questioned in menswear, with the masculine ideal continually reimagined to create a balance between itself and its counterpart, femininity. During the 1980s AIDS crisis, this adopted uniform of masculinity was subverted within queer society leading to a new male identity that contested tacit knowledge of menswear design. The focus of this article is to showcase this shift in male image and to explore how gay semiotics was associated with the development of the modern gay male stance through clothing and social empowerment, opposing the negativity that surrounded the AIDS virus. This research is personally motivated by the primary author, where he seeks to delve further into the under-researched area of queer masculinity utilizing a practical, experimental methodology. Representation of what is seen as queer masculinity is often shown as biased within society, characterizing the gay man. This project presents, through the practices of menswear design, how this characterization has developed within the context of the male body. It aims to contest the boundaries of traditional men’s tailoring, its formality and the masculine ideal that it represents, by juxtaposing it with the homoerotic art of the time and the craft of AIDS sufferers of the 1980s period. Using object-study and practical methods of deconstruction and repair of case study (bespoke and non-bespoke) men’s tailored jackets, the research manifests in physical experimentation and aesthetic visualization, which is recorded in a creative process journal. The acts of physical deconstruction and the practice of repair are then analysed through the process of design development (drawing, sourcing and sampling). The synthesized findings draw parallels with deconstructed tailoring found in vintage photographs of men at work, which are further triangulated with homoerotic photographic art of the 1980s and the act of repair found in the stitch therapy of AIDS sufferers. These are embedded in the construction of the final artefact through the practice of garment design (drawing, pattern-cutting, toiling and making) and craftsmanship (stitching by hand). The processes employed and final artefact produced document and present how ideals of masculinity in the time of AIDS can be both physically and metaphorically deconstructed, then reconstructed as a garment-based outcome (men’s tailored jacket) in practice-led research. The final artefact showcases delicacy in design through the act of stitching by hand and the repair of the deconstructed robust exteriors found in tailoring and associated with the masculine ideal.