This interdisciplinary paper will explore the important gendered meanings of the British wool textile designs that were widely used to make the tailored clothes adopted by men and women between the 1870s and 1914. Seminal wool textile designs that developed in the nineteenth century, such as the Glen Urquhart check, often known as the Prince des Galles check, were originally strongly coded as masculine, yet they came to be highly significant within both men and women’s fashion. The Glen Urquhart check continues to form one of Les Tissus Masculins used by Christian Dior today. This paper builds on and extends previous research for the book Tweed by using a methodology that investigates the meanings of tailored clothing in wool textiles from the raw fibre to the finished garment. It will argue that wearing tailored clothing was a cultural and social practice that related to a wide spectrum of gender identities, and it constituted a pivotally important space of fluidity and change. The paper will demonstrate the varied strategies undertaken by women to address the conflicting notions of freedom, transgression, modernity, practicality and fashion linked to wearing tailored wool garments. In particular, it will contest the idea that women wearing tailored clothing always challenged existing gendered social and sartorial codes between 1870 and 1914. These arguments will include exploring wool textile design as a highly nuanced area of change and fluidity in relation to gendered meanings, which demonstrates how notions of acceptable ‘masculine’ and ‘feminine’ appearances were constantly being re-interpreted in the late nineteenth century. Significantly, comparisons with the colours, patterns and textures of the wool textiles used for men’s tailoring will demonstrate that codes of masculinities and femininities were subtle, unstable and subject to flux in that era.