Summary: Patients with maxillomandibular disharmony may present with a flat to concave midface. The effects of orthognathic surgery concomitant with midface fat grafting on facial appearance and midface volumetric and positional change have not formally been assessed to date. The authors’ approach for synchronous orthognathic surgery and fat grafting is described and evaluated. Adult female patients (n = 20) who underwent synchronous two-jaw orthognathic surgery and cheek-specific fat grafting (1.9 ± 0.6 cm3 per side) for correction of skeletal class III deformity and anteromedial cheek deficiency were prospectively included. Preoperative and postoperative photographs were appraised by 42 blinded raters using facial appearance scales for beauty, attractiveness, and pleasantness parameters. The three-dimensional midface soft-tissue volume change and postoperative cheek mass position were computed. Facial imaging data from gender-, ethnic-, and facial pattern–matched adult patients (n = 20) who underwent isolated two-jaw orthognathic surgery (n = 20) were included for comparison. The three-dimensional facial norms database–derived cheek mass position information (2.19 ± 1.31mm) was also adopted for analysis. Patients treated with the synchronous procedure had significantly (p < 0.001) increased facial appearance–related perception change for beauty (2.9 ± 1.6), attractiveness (2.8 ± 1.8), and pleasantness (3.0 ± 1.5) parameters, three-dimensional midface volume change (1.8 ± 0.5 cm3), and postoperative cheek mass position (2.16 ± 0.47 mm) in comparison with those treated with the isolated procedure (2.0 ± 1.5, 1.9 ± 1.6, 2.3 ± 1.6, 0.6 ± 0.2 cm3, and 1.84 ± 0.43 mm, respectively). Healthy female individuals had similar and larger cheek mass position than patients treated with synchronous (p > 0.05) and isolated (p < 0.001) procedures, respectively. Synchronous orthognathic surgery and check-specific fat grafting resulted in superior enhancement of facial appearance and midface volume and position compared with isolated orthognathic surgery. CLINICAL QUESTION/LEVEL OF EVIDENCE: Therapeutic, III.