Hypertrophic scars (HS) are considered to be the greatest unmet challenge in wound and burn rehabilitation. The most common treatment for HS is pressure therapy, but pressure garments may not be able to exert adequate pressure onto HS due to the complexity of the human body. However, the development of three-dimensional (3D) scanning and direct digital manufacturing technologies has facilitated the customized placement of additively manufactured silicone gel onto fabric as a component of the pressure therapy garment. This study provides an introduction on a novel and customized fabrication approach to treat HS and discusses the mechanical properties of 3D printed fabric reinforced with a silicone composite. For further demonstration of the suggested HS therapy with customized silicone insert, silicone inserts for the finger webs and HS were additively manufactured onto the fabric. Through the pressure evaluation by Pliance X system, it proved that silicone insert increases the pressure exerted to the HS. Moreover, the mechanical properties of the additively manufactured fabric silicone composites were characterized. The findings suggest that as compared with single viscosity print materials, the adhesive force of the additively manufactured silicone and fabric showed a remarkable improvement of 600% when print materials with different viscosities were applied onto elevated fabric.