Robots could be a valuable tool for helping with dressing but determining how a robot and a person with disabilities can collaborate to complete the task is challenging. We present task optimization of robot-assisted dressing (TOORAD), a method for generating a plan that consists of actions for both the robot and the person. TOORAD uses a multilevel optimization framework with heterogeneous simulations. The simulations model the physical interactions between the garment and the person being dressed, as well as the geometry and kinematics of the robot, human, and environment. Notably, the models for the human are personalized for an individual’s geometry and physical capabilities. TOORAD searches over a constrained action space that interleaves the motions of the person and the robot with the person remaining still when the robot moves and vice versa. In order to adapt to real-world variation, TOORAD incorporates a measure of robot dexterity in its optimization, and the robot senses the person’s body with a capacitive sensor to adapt its planned end effector trajectories. To evaluate TOORAD and gain insight into robot-assisted dressing, we conducted a study with six participants with physical disabilities who have difficulty dressing themselves. In the first session, we created models of the participants and surveyed their needs, capabilities, and views on robot-assisted dressing. TOORAD then found personalized plans and generated instructional visualizations for four of the participants, who returned for a second session during which they successfully put on both sleeves of a hospital gown with assistance from the robot. Overall, our work demonstrates the feasibility of generating personalized plans for robot-assisted dressing via optimization and physics-based simulation.