The intriguing multi-scale fractal patterns ubiquitously observed in nature similarly emerge as fascinating structures in two-phase fluid flows of bio-oil breakup and atomization processes. High-resolution microscopy of the two-phase flows under 15 flow conditions (cases of different flow rates of the liquid and co-flowing air streams as well as different degrees of liquid preheating) reveal that the geometrical complexities evolve under the competing/combined action of the instability mechanisms such as Kelvin–Helmholtz, Rayleigh–Taylor and Rayleigh–Plateau leading into the transition from break-up to atomization. A thorough analysis of the higher order moments of statistics evaluated based on the probability density functions from 15,000 fractal dimension samples suggest that a single-value analysis is not sufficient to describe the complex reshaping mechanisms in two-phase flows. Consistently positive skewness of the statistics reveal the role of abrupt two-phase mechanisms such as liquid column rupture, ligament disintegration, liquid sheet bursting and droplet distortions in a hierarchical geometrical entanglement. Further, large kurtosis values at increased flow inertia are found associated with turbulence-induced intermittent geometrical reshaping. Interestingly, the proposed power-law correlation reveals that the global droplet size obtained from laser-diffraction measurements declines as the two-phase geometrical complexity increases.