Land surface temperature (LST) is a fundamental physical quantity in a range of different studies, for example in climatological analyses and surface–atmosphere heat flux assessments, especially in heterogeneous and complex surfaces such as vegetated canopies. To obtain accurate LST values, it is important to measure accurately the land surface emissivity (LSE) in the thermal infrared spectrum. In the past decades, different directional emissivity canopy models have been proposed. This paper evaluates six radiative transfer models (FR97, Mod3, Rmod3, 4SAIL, REN15, and CE-P models) through a comparison with in situ emissivity measurements performed using the temperature-emissivity separation (TES) method. The evaluation is done using a single set of rose plants over two different soils with very different spectral behavior. First, using an organic soil, the measurements were done for seven different observation angles, from 0° to 60° in steps of 10°, and for six different values of leaf area index (LAI). Taking into account all LAIs, the bias (and root mean square error, RMSE) obtained were 0.003 (±0.006), −0.004 (±0.005), −0.009 (±0.011), 0.005 (±0.007), 0.004 (±0.007), and 0.005 (±0.007) for FR97, Mod3, Rmod3, 4SAIL, REN 15, and CE-P models, respectively. Second, using an inorganic soil, the measurements were done for six different LAIs but for two different observation angles: 0° and 55°. The bias (and RMSE) obtained were 0.012 (±0.014), 0.004 (±0.007), −0.020 (±0.035), 0.016 (±0.017), 0.013 (±0.015), 0.013 (±0.015) and for FR97, Mod3, Rmod3, 4SAIL, REN15, and CE-P models, respectively. Overall, the Mod3 model appears as the best model in comparison to the TES emissivity reference measurements.