We report experimental and particle-based kinetic simulation studies of low-pressure capacitively coupled oxygen plasmas driven by tailored voltage waveforms that consist of up to four harmonics of base frequency 13.56 MHz. Experimentally determined values of DC self-bias and electrical power deposition, as well as flux density and flux-energy distribution of the positive ions at the grounded electrode are compared with simulation data for a wide range of operating conditions. Very good agreement is found for self-bias and flux-energy distribution of the positive ions at the electrodes, while a fair agreement is reached for discharge power and ion flux data. The simulated spatial and temporal behaviour of the electric field, electron density, electron power absorption, ionization rate and mean electron energy shows a transition between sheath expansion heating and drift-ambipolar discharge modes, induced by changing either the number of harmonics comprising the excitation waveform or the gas pressure. The simulations indicate that under our experimental conditions the plasma operates at high electronegativity, and also reveal the crucial role of singlet metastable molecules in establishing discharge behavior via the fast destruction of negative ions within the bulk plasma.