Virtual prototyping practice and technologies are developing fast and moving from the traditional industrial sectors that have pushed their development (automotive, aeronautical) to new sectors, like the fashion sector, that is far from them, but anyway economically important. The concept of Virtual Prototyping has been built upon a bottom up approach. Tools oriented to different phases of the product development process (CAD, CAM, CAE, etc.) have been developed separately, without any intersection or anything in common among them, except for the idea that the geometrical model of the object is the reference point for the all phases. Actually, each of these tools simulates a single aspect/characteristic of the future product: the shape, the appearance, the manufacturability, the strain, the physical behaviour, etc. On top of them, Virtual Prototyping was developed with multiple aims. First, it aimed at integrating into a unique "object" all the characteristics that are uniquely formalised, and that can be uniquely simulated, so allowing an integration of all the interrelations among the all product aspects. Another characteristic of Virtual Prototyping concerns its use in validation. This has raised the need to make compatible the context where the prototype can or could be virtually operating, in terms of digital modelling. Therefore, the Virtual Prototype can be seen as a correlated set of dedicated models able to simulate specific aspects and models of interaction modalities. The paper presents the key aspects of Virtual Prototyping and enabling technologies in the fashion sector, presenting their benefits and the shortcomings that still require research and development.