Three-dimensional (3D) deformity assessment and leg realignment planning is emerging. The aim of this study was to (1) validate a novel 3D planning modality that incorporates the weight-bearing (WB) state (3D WB) by comparing it to existing modalities (3D non-weight-bearing (NWB), 2D WB) and (2) evaluate the influence of the modality (2D vs. 3D) and the WB condition on the measurements. Three different planning and deformity measurement protocols were analyzed in 19 legs that underwent medial open-wedge high tibial osteotomy (HTO): (1) a 3D WB protocol, after 2D/3D registration of 3D CT models onto the long-leg radiograph (LLR) (3D WB), (2) a 3D NWB protocol based on the 3D surface models obtained in the supine position (3D NWB), and (3) a 2D WB protocol based on the LLR (2D WB). The hip–knee–ankle angle (HKA), joint line convergence angle (JLCA), and the achieved surgical correction were measured for each modality and patient. All the measurement protocols demonstrated excellent intermodal agreement for the achieved surgical correction, with an ICC of 0.90 (95% CI: 0.76–0.96)) (p < 0.001). Surgical correction had a higher mean absolute difference compared to the 3D opening angle (OA) when measured with the WB protocols (3D WB: 2.7 ± 1.8°, 3D NWB: 1.9 ± 1.3°, 2D WB: 2.2 ± 1.3°), but it did not show statistical significance. The novel planning modality (3D WB) demonstrated excellent agreement when measuring the surgical correction after HTO compared to existing modalities.