The Shenzhen Electronics Group (SEG) Plaza in Shenzhen, China, experienced visible vibrations attributed to significant vortex-induced vibrations of the large spacing twin-mast atop the building. The vibration event occurred under complex urban wind environments. In order to reproduce wind fields around SEG Plaza, a multiscale simulation was carried out by integrating the Weather Research and Forecasting (WRF) and Computational Fluid Dynamics (CFD) models. The aerodynamic characteristics and wake modes of twin-mast are investigated by a downscale CFD simulation in detail. Finally, vortex-induced vibration (VIV) of twin-mast was analyzed considering fluid-structure interaction. This work reveals that wind conditions during the SEG Plaza vibration incident were appropriate for the VIV occurrence of twin-mast, and the results of VIV simulation agree well with the field monitoring results by computer vision identification. This study effectively reproduces the full pictures of VIVs of the rooftop twin-mast during this rare event, offering a critical view for the analysis of this event.