Fractal structures pervade nature and are receiving increasing engineering attention towards the realization of broadband resonators and antennas. We show that fractal resonators can support the emergence of high-dimensional chaotic dynamics even in the context of an elementary, single-transistor oscillator circuit. Sierpiński gaskets of variable depth are constructed using discrete capacitors and inductors, whose values are scaled according to a simple sequence. It is found that in regular fractals of this kind each iteration effectively adds a conjugate pole/zero pair, yielding gradually more complex and broader frequency responses, which can also be implemented as much smaller Foster equivalent networks. The resonators are instanced in the circuit as one-port devices, replacing the inductors found in the initial version of the oscillator. By means of a highly simplified numerical model, it is shown that increasing the fractal depth elevates the dimension of the chaotic dynamics, leading to high-order hyperchaos. This result is overall confirmed by SPICE simulations and experiments, which however also reveal that the non-ideal behavior of physical components hinders obtaining high-dimensional dynamics. The issue could be practically mitigated by building the Foster equivalent networks rather than the verbatim fractals. Furthermore, it is shown that considerably more complex resonances, and consequently richer dynamics, can be obtained by rendering the fractal resonators irregular through reshuffling the inductors, or even by inserting a limited number of focal imperfections. The present results draw attention to the potential usefulness of fractal resonators for generating high-dimensional chaotic dynamics, and underline the importance of irregularities and component non-idealities.The morphology of diverse natural objects is knowingly self-similar across levels of scale. This feature, referred to as fractality, is observed for example in the shape of coastlines, vegetables, single neurons and even entire brains. Its origin, albeit often ultimately elusive, has at times been ascribed to certain dynamical properties such as operation close to a critical point. On the other hand, comparatively limited attention has been given to the impact that the presence of fractal structure can in itself have on the dynamics of a non-linear system. Since