The current work investigates the suitability of seven contestant formulations toward the development of a green commercial lipstick model incorporated with vitamin D3. We analytically examined their thermal, mechanical, diffusion, and skin hydration characteristics using differential scanning calorimetry, oscillatory shear rheology, in vitro release tests, and skin capacitance measurements. In the process, we methodically studied the material properties of wax-based natural cosmetic formulations, as well as ways to improve on an existing standard industrial lipstick formulation. We note that the type of the constituent wax, rather than its concentration, produces noteworthy influence on nearly all characterization parameters. The results suggest that a combination of berry wax, candelilla wax, and carnauba wax could be used as an effective formulation base toward the realization of a lipstick supplemented with vitamin D3. This specific wax combination offers the possibility of combining the advantages of sustainability as well as health benefits in a lipstick formulation. In the future, an independent tribological study, an investigation of natural enhancers to accelerate transdermal vitamin D3 penetration, as well as a large-scale sensory evaluation of the formulations developed here could be carried out. This would help establish a wholesome optimized lipstick model that could be fast-tracked for a commercial launch.