Shale oil reservoirs are characterized by having various types of vertical sublayers, a large contrast in rock mechanical properties, well-developed bedding, and high clay content, which are likely to cause rock elastic–plastic deformation. In numerical simulations of hydraulic fracture (HF) propagation in the shale oil reservoirs, the effects of rock elastic–plastic deformation and complex bedding structure on the layer-crossing behavior of HF are not considered. To understand the mechanism of HF height growth in shale oil reservoirs, we used the cohesive zone method to establish an elastic–plastic finite element model of HF propagation by considering the effects of shell limestone interlayers, the Mohr–Coulomb yield criterion for shear–plastic failure, the cross-mechanical interaction between bedding and shale oil reservoir, and the complex situations such as the HF height across high-electrical resistivity bedding and high-conductivity fractures. The effects of internal friction angle, cohesion, layer stress contrast, fracture toughness, bedding bond strength, injection rate, elastic modulus, and bedding shear strength on HF height growth in shale oil reservoirs are studied, and the characteristics of HF width profile, injection pressure, failure mode, and maximum HF width are compared. Compared with the layer stress contrast, cohesion, internal friction angle, and fracture toughness, the injection rate, elastic modulus, and bedding shear strength and bond strength have a larger effect on the vertical HF width. Increment of the injection rate, decrease of the elastic modulus, and increment of the bedding shear strength and bond strength are favorable for HF height growth in the shale oil reservoir. As rock cohesion and internal friction angle increase, the HF width decreases. At the initial stage of fracturing fluid injection, the maximum HF height and injection pressure fluctuate. Lower cohesion and internal friction angle promote rock shear failure in HF height growth. Our study provides guidance for the stimulation of fracture crossing layers in the shale oil reservoirs.