The Dissertation here presented pretends to analyse and characterize the most creative sector of Portuguese Textile and Apparel Industry: Portuguese Fashion Design. Today, Textile and Apparel Industry is one of the most important cluster of Portugal economy. However, this industry, did not always give the right importance to factors such as Creativeness, Innovation and Design as a way of reach competitive advantages in international markets. In a nutshell, Portuguese Fashion Design, despite difficult periods and constrains, has been able to reveal a continuously growth and respect on international markets. Obviously, we hear today about the successful investments by Textile and Apparel Industry on improvement, development and innovation as a strategic response to market demands or requirements. Fashion World is particularly known by its quick change and where the new ideas, new ways of doing things, new products and services of today will be obsoleted tomorrow. Under fast-changing environments, players need to adopt measures and strategies to fight back market demands and heavy competition in order to survive. With this, it is up to Portuguese Fashion Designers along with Textile and Apparel Industry to seek constant alternatives and opportunities to reach a high level of competitiveness and to keep up with market demands. Back to this dissertation, the comparison between three Portuguese fashion players based on news and interviews make it possible the analysis of Portuguese Fashion Design’s evolution and to draw guidelines about its future journey.