The Land Surface Temperature (LST) is well suited to monitor biosphere–atmosphere interactions in forests, as it depends on water availability and atmospheric/meteorological conditions above and below the canopy. Satellite-based LST has proven integral in observing evapotranspiration, estimating surface heat fluxes and characterising vegetation properties. Since the radiative regime of forests is complex, driven by canopy structure, components radiation properties and their arrangement, forest radiative temperatures are subject to strong angular effects. However, this depends on the scale of observation, where scattering mechanisms from canopy – to satellite – scales influence anisotropy with varying orders of magnitude. Given the heterogeneous and complex nature of forests, multi-angular data collection is particularly difficult, necessitating instrumentation distant enough from the canopy to obtain significant canopy brightness temperature and concurrent observations to exclude turbulence/atmospheric effects. Accordingly, current research and understanding on forest anisotropy at varying scales (from local validation level to satellite footprint) remain insufficient to provide practical solutions for addressing angular effects for upcoming thermal satellite sensors and associated validation schemes. This study presents a novel method founded in the optical remote sensing domain to explore the use of microcanopies that represent forests at different scales in the footprint of a multi-angular goniometer observing system. Both Geometric Optical (GO) and volumetric scattering dominated canopies are constructed to simulate impacts of anisotropy in heterogeneous and homogeneous canopies, and observed using a thermal infrared radiometer. Results show that heterogeneous canopies dominated by GO scattering are subject to much higher magnitudes of anisotropy, reaching maximum temperature differences of 3 °C off-nadir. Magnitudes of anisotropy are higher in sparse forests, where the gap fraction and crown arrangement (inducing sunlit/shaded portions of soil and vegetation) drive larger off-nadir differences. In dense forests, anisotropy is driven by viewing the maximum portion of sunlit vegetation (hotspot), where the soil is mostly obscured. Canopy structural metrics such as the fractional cover and gap fraction were found to have significant correlation with off-nadir differences. In more homogeneous canopies, anisotropy reaches a lower magnitude with temperature differences up to 1 °C, driven largely by volumetric scattering and components radiation properties. Optimal placement of instrumentation at the canopy-scale (more heterogeneous behaviour due to proximity to the canopy and small pixel size) used to validate satellite observations (more homogeneous behaviour due to larger pixel size) was found to be in cases of viewing maximum sunlit vegetation, for dense canopies. Given upcoming high spatial resolution sensors and associated validation schemes needed to benchmark LST and downstream products such as evapotranspiration, a better understanding of anisotropy over forests is critical to provide accurate, long-term and multi-sensor products.