A simple process to clad conventional monofilament fibers with low‐molecular‐weight liquid crystals (LCs) stabilized by an outer polymer sheath is demonstrated. The fibers retain the responsive properties of the LCs but in a highly flexible/drapable format. The monofilament core makes these fibers much more rugged with a magnified response to external stimuli when compared to previously reported LC‐core fibers produced by electrospinning or airbrushing. The microscopic structure and the optical properties of round and flattened fibers are reported. The sensitivity of the response of individual fibers can be tuned over a broad range by varying the composition of the LCs. Complex fabrics can be easily woven from fibers that respond to different external stimuli, such as temperature variation, chemical concentrations, and pressure. The fabrics can be fashioned into garments that can sense and report the state of health of the wearer or the status of their environment. The first successful incorporation of low‐molecular‐weight liquid crystals as a responsive cladding on conventional monofilament fibers is reported. The fibers can be easily woven into textiles and fashioned into garments that can sense and report factors such as temperature, pressure, and chemical vapor content.