This updates a longitudinal study of Bespoke/ High End tailoring (Ross, 2007) with a secondary focus on mid-market menswear. The discussion commences with a review of key literature and practices from digital menswear studies to-date and evaluates how in the last two decades a deeply entrenched traditional sector such as tailoring has embraced numerous fashion digital-technologies from the design process to multi-channel consumption in-store, e-commerce and apps. The author utilizes a 3D-4C's process model as a structural template. The research methodology is interpretive, qualitative, online structured-observation of tailors currently utilizing digital practices plus in-depth interviews with industry experts. Those interviewed include Bespoke/Designer tailors with current 3D- platforms and International researchers providing insight into the latest developments in digital fashion including virtual design, scanning, sizing, avatars, 3D-fabric-simulations, 3D-printing, virtual-try-on and customization to establish best practices and future forecasts for proactive fashion management.