Purpose: Dental esthetics has increasingly become an important and rewarding discipline in dentistry as patients have begun to request anterior restorations of high esthetic quality. Clinicians must be prepared to meet the esthetic demands and high expectations of their patients. Different variables may influence the esthetic quality of restorations. Quality evaluations may vary with clinical or patient assessments. This study attempted to assess the esthetic quality of maxillary anterior restorations in order to determine the percentage of restorations with satisfactory quality, examine variables affecting esthetic quality, and make comparisons between agreements and disagreements in clinical and patient evaluations. Materials and Methods: Restorations in patients attending different dental clinics in Irbid, Jordan were examined. Clinicians compared the color and shape of the restorations with those of a natural tooth using Ryge criteria, and patients evaluated the same parameters and the surface texture using a Visual Analogue Scale (VAS). Evaluations ranked the quality as good, satisfactory, or poor. Results: The percentage of esthetic complaints was 32.4%, whereas the percentage of satisfactory restorations revealed was 43.8% and 67.6% by clinical and patient assessments, respectively. Restorations yielded significantly better scores on both evaluations when they were prepared by dental students, made in the Dental Teaching Centre (DTC), or were less than one year old. The number of agreements between clinical and patient rankings was significantly less than disagreements. Conclusions: There were statistically significant disagreements on the esthetic quality between clinicians and patients. Age, gender, practice sector, qualification of the operator, type, and longevity of restoration significantly affected the assessments.