This paper studies the evolvement of the wear irregularity of contact wire using wire thickness data measured yearly from a section of railway catenary. The power spectral density and time–frequency representation based on the wavelet transform are employed for data analysis, with an emphasis on local wear irregularities that are crucial for contact wire condition assessment. To investigate the cause of wear irregularity evolvement and the mutual influence with the pantograph–catenary dynamic interaction, simulations considering the influence of wear irregularity are carried out based on the finite element method. Analyses of the actual wear irregularities and the dynamic contact force under singular and complex wear irregularities are performed. Although the wear irregularity has limited impact on the pantograph–catenary interaction, it can induce the vibration of pantograph and contact wire that will lead to a notable increase of contact force standard deviation. The evolvement of wear irregularity is closely associated with the span length and dropper distribution of catenary structure and the running direction of pantograph. In addition, it is found feasible to detect the wear irregularity based on contact force, on condition that the sampling frequency is high enough to reflect the indicative frequencies.