This article explores the cut, construction and silhouette of early nineteenthcentury men's coats as a methodology for the development of contemporary womenswear. This practice-based research focuses on aspects of bespoke tailoring between the late eighteenth and twenty-first centuries, with a specific interest in the period between 1820 and 1845, examining how the forms and shapes of the garments were achieved through methods of construction, and how these, in turn, helped to shape discourses surrounding gender narratives. Christian Dior and Vivienne Westwood designs have been selected as examples of womenswear that were shaped by historical forms, tailoring and notions of gender. In order to explore how the techniques of men's tailoring can be translated into a contemporary women's garment, a woman's jacket, drawing on elements of historical design, construction and bespoke tailoring methods, was produced by the author. The very feminine form, with an emphasis on sharp shoulders, narrow waist and wide skirt, captures the hourglass shape found in men's tail and frock coats of the early nineteenth century as well as Christian Dior and Vivienne Westwood's tailored garments. The past and the present are thereby brought together through bespoke tailoring.