In this work we report on the processing, melt-drawing, and performance of new vanillic acid based aliphatic-aromatic thermotropic polyesters. It is demonstrated that these materials are easily processed from their nematic melts yielding highly oriented products. Furthermore, we demonstrate that a molecular weight (Mw) of roughly 30 kg/mol is required in order to successfully perform spinning on these polymers. The application of a polymer with lower Mw results in poor mechanical performance and fiber breakage during the winding process. Wide-angle X-ray diffraction analysis has been performed on the fibers and it is demonstrated that the orientation parameter increases with increasing draw-ratio of the fiber. Although these polymers are readily processed from their thermotropic melts, the obtained fibers only retain their orientation up to temperatures in the range of 120–130 °C, after which they start to melt. In general, these fibers exhibit tensile moduli in the range of ~10 GPa and a tensile strength around ~150 – 200 MPa. FTIR and solid-state NMR experiments indicate that only the aromatic components are molecularly oriented during the spinning process. In contrast, the aliphatic moieties exhibit a high mobility, normally corresponding to a local isotropic motion. It is expected that the poor molecular orientation of the aliphatic moieties in these aliphatic-aromatic thermotropic polyesters contribute to the relatively low tensile modulus of the fibers, obtained after the extrusion and melt-drawing process.