The paper deals with the theoretical and fundamental conceptual foundation of new forms of work arrangements, i.e. so-called “platform work”, considering its practical application. The idea of matching the supply and demand for paid work through an online platform in the era of “platform capitalism” creates several legal discrepancies calling for urgent policy and legal answers. In the paper, we aim to analyse the so-called “platform work”, which is staying halfway between traditional subordinate work and self-employment, by applying the legal normative and comparative method, along with the holistic approach to the research subject regarding the identification of its legal nature. The standard elements of the employment relationship – a contract-based relation, the performance of work on another’s behalf, payment of remuneration and subjection to direction and supervision i.e. subordination – need to be considered in terms of the technological changes, transformations in the organisation of companies and, consequently, the flexibility of work arrangements. The importance of adjustment of the labour law theory and practice to a new reality by addressing the “products” of the gig economy represented in new digital forms of work supports the principles of social justice, equity, and dignity at work. The labour law needs to follow changes in the economy and society by expanding the scope of its core concepts to address the regulatory gaps and perform its mission of protection of employment-related rights and freedoms.