Additive manufacturing (AM) technologies enable the production of customized and personalized medical devices that facilitate users’ comfort and rehabilitation requirements according to their individual conditions. The concept of a tailor-made orthopedic device addresses the accelerated recovery and comfort of the patient through the utilization of personalized rehabilitation equipment. Direct modeling, with an increasing number of approaches and prototypes, has provided many successful results until now. The modeling procedure for 3D-printed orthoses has emerged as the execution of steady and continuous tasks with several design selection criteria, such as cutting, thickening the surface, and engraving the shell of the orthosis. This publication takes into consideration the aforementioned criteria and proposes the creation of a holistic methodology and automated computational design process for the customization of orthotic assistive devices, considering aspects such as material properties, manufacturing limitations, recycling, and patients’ requirements. This proposal leads to the designing and manufacturing of a wrist orthopedic device based on reverse engineering, Design for AM (DfAM), and Design for Recycling (DfR) principles. The proposed methodology can be adjusted for different limbs. A dual-material approach was attained utilizing rigid, mechanically enhanced feedstock material and soft elastic material with reduced skin irritation risks to achieve both mechanical requirements and adequate cushioning for user comfort during rehabilitation. Recyclable thermoplastic matrices were selected, which also allow for the option to create washable devices for product life extension. Then, 3D scanning procedures were implemented to acquire the initial anatomic measurements for the design of the WHO and ensure and assess the dimensional accuracy of the final product. Physical mechanical testing was implemented to evaluate the WHO’s mechanical behavior and verify its functionality during basic wrist movements. The extracted dimensional data for the two main orthosis components that indicated approximately 50% and 25% of the tolerance values, respectively, were within the range (−0.1 mm, 0.1 mm).