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Cholesteryl ester liquid crystals exhibit thermochromic properties related to the existence of a twisted nematic phase. We formulate ternary mixtures of cholesteryl benzoate (CB), cholesteryl pelargonate (CP), and cholesteryl oleyl carbonate (COC) to achieve thermochromic behavior. We aim to achieve thermochromic fibers by incorporating the liquid crystal formulations into electrospun fibers. Two methods of incorporating the liquid crystal (LC) are compared: (1) blend electrospinning and (2) coaxial electrospinning using the same solvent system for the liquid crystal. For blend electrospinning, intermolecular interactions seem to be important in facilitating fiber formation since addition of LC can suppress bead formation. Coaxial electrospinning produces fibers with higher nominal fiber production rates (g/hr) and with higher nominal LC content in the fiber (wt. LC/wt. polymer assuming all of the solvent evaporates) but larger fiber size distributions as quantified by the coefficient of variation in fiber diameter than blend electrospinning with a single nozzle. Importantly, our proof-of-concept experiments demonstrate that coaxially electrospinning with LC and solvent in the core preserves the thermochromic properties of the LC so that thermochromic fibers are achieved.