Condition monitoring (CM) is the basis of prognostics and health management (PHM), which is gaining more and more importance in the industrial world. CM, which refers to the tracking of industrial equipment's state of health during operations, plays, in fact, a significant role in the reliability, safety, and efficiency of industrial operations. This paper proposes a data-driven CM approach based on the autoregressive (AR) modeling of the acquired sensor data and their analysis within frequency subbands. The number and size of the bands are determined with negligible human intervention, analyzing only the time-frequency representation of the signal of interest under normal system operating conditions. In particular, the approach exploits the synchrosqueezing transform to improve the signal energy distribution in the time-frequency plane, defining a multidimensional health indicator built on the basis of the AR power spectral density and the symmetric Itakura-Saito spectral distance. The described health indicator proved capable of detecting changes in the signal spectrum due to the occurrence of faults. After the initial definition of the bands and the calculation of the characteristics of the nominal AR spectrum, the procedure requires no further intervention and can be used for online condition monitoring and fault diagnosis. Since it is based on the comparison of spectra under different operating conditions, its applicability depends neither on the nature of the acquired signal nor on a specific system to be monitored. As an example, the effectiveness of the proposed method was favorably tested using real data available in the Case Western Reserve University (CWRU) Bearing Data Center, a widely known and used benchmark.