The challenge surgeons face when reconstructing cheek defects varies significantly depending on the location and depth of the defect and the distensibility of the surrounding tissues. The cheek is a large aesthetic unit characterized in most areas with a convex surface and inherent transitions in color and texture. These characteristics demand the surgeon’s attention to achieve superior results during reconstruction. Surgeons must also recognize the free margins of the adjacent structures, including the lower eyelid, nasal ala, and lip, to minimize distortion of these areas during healing. With these challenges in mind, this article discusses several approaches to reconstruction of various types of cheek defects.