Tire rolling deformation consists of valuable information for vehicle control and tire development applications. To gain insight into this deformation, both model-based and tire sensor-based approaches have been investigated in previous studies. However, existing tire models oversimplified the pressure distribution in the tire-road contact due to a lack of related experiment data especially for deformations of the tire at high rolling speeds. Meanwhile, the tire sensing method requires extensive experiments and cannot be directly used within vehicle simulations. For resolving the above issues, this paper proposes a combined approach for studying tire rolling deformation. Specifically, the flexible ring tire model (FRTM) is extended with a realistic, dynamic pressure distribution to provide more accurate predictions of the rolling tire deformation under various operation conditions. Meanwhile, a three-dimensional high-speed stereo vision system has been set up together with an optimized digital image correlation (DIC) method to measure the deformation of high-speed rolling tires. The experimental results reveal that rolling tires experience an eccentric deformation and an anti-symmetric deformation in the radial and tangential directions, respectively. Additionally, it was observed that the vertical load has a more substantial influence than the tire pressure on rolling deformation. The capability of the improved ring tire model to describe these observed phenomena has been validated through comparisons between simulations and measurements.