Hairpin windings are seeing an ever-increasing application and development in electrical machines designed for high power and torque densities. In fact, due to their inherently high fill factor, they are very attractive in applications, such as transportation, where these characteristics are considered main design objectives. On the other hand, high operating frequencies also contribute to improve power density of electrical machines. However, at high fundamental frequencies, hairpin windings are characterised by increased Joule losses due to skin and proximity effects. Hence, while these technologies are introducing new opportunities, a number of challenges still need to be addressed. These include manufacturing aspects, contacting processes, thermal management, etc. This paper presents an overview of the current state-of-the-art of hairpin technologies and propose possible future opportunities. The authors' perspective is then finally provided, showing how innovative winding patterns can potentially overcome the above mentioned challenges.