Abstract: A system for cooling a head of a user to mitigate or prevent drug-induced hair-loss, including a hat, which includes an exterior layer, an interior layer, with an inflatable chamber therebetween, the inflatable chamber being functionally associated with an inflation pump. The hat includes a cooling assembly, reversibly attachable to the interior layer and including a housing defining pockets having cooling pads therein. Each cooling pad comprising a phase-changing-material adapted to obtain a temperature lower than ?20° C. and to retain that temperature. A sensor is adapted to sense an environmental condition within the hat. A controller is adapted to receive input from the sensor, and to provide a notification when the sensed environmental condition is outside of a specific range. When the hat is donned by the user, the inflatable chamber is inflated sufficiently to ensure that the cooling assembly engages the scalp of the user.