This study had investigated the solubility of p-methylbenzyl alcohol (PMAL) by the static equilibrium method. Solubility data were determined in six common alcoholic solvents (methanol, ethanol, n-propanol, i-propanol, n-butanol, i-butanol) and non-alcoholic solvents (acetone, acetonitrile, ethyl formate, ethyl acetate, dichloromethane, 1,2-dichloroethane) over a temperature range of 278.15–313.15 K. The effect of temperature on PMAL solubility was significant in both solvent types, particularly in acetonitrile. Six thermodynamics models were employed to correlate the solubility data, with the modified Apelblat equation providing the best fit. The study also analyzed the factors influencing PMAL solubility by integrating the physicochemical properties of the solvents with Density Functional Theory calculations. The result suggested that multiple factors affect PMAL solubility in both solvent categories. Additionally, the electrostatic potential energy surfaces and the solvent–solute interaction energies were calculated based on Density Functional Theory. The order of interaction energies correlated with solubility trends. The calculated apparent thermodynamic properties, derived from the Van’t Hoff equation, revealed that the dissolution process was entropy-driven with heat absorption.