Moisture handling property of fabric has been regarded as a major factor in the comfort performance of clothing in normal use. Especially in different environmental temperature conditions, fabric’s moisture comfort property has different manifestation. In this paper, a series of experiments and analyses were performed on studying the dynamic moisture transferring procedure and evaluating moisture comfort property of fabric under different environmental temperature conditions. By Textile-Microclimate Measuring Instrument, five different fiber fabrics’ dynamic experiments were performed in different environmental temperature conditions. By measuring the real time changes of relative humidity in inner and outer surfaces of test fabrics, fabrics’ dynamic comprehensive index was obtained to characterize fabrics’ dynamic moisture comfort property under different temperature conditions. Finally, grey system theory was introduced to establish models that could describe the relationship between the static parameters and the dynamic comprehensive index. The grey interrelationship analysis was performed firstly to find out the static parameters that have high degree of association with dynamic comprehensive index. And then the grey mathematics modeling method was performed to establish models predicting the dynamic comprehensive index using static parameters. In three different temperature conditions, three different prediction models were built and high predictive precision was obtained.