Shade matching is an essential procedure to obtain an esthetic prosthesis. The Direct Visual Shade Matching (DSM) method using shade guides is the most used method by dentists. However, The Indirect Visual Digital Shade Matching (ISM) method based on digital imaging is concerned to be reliable and useful in determining shade matching in dental practice. Several factors such as method, clinical experience, and gender can affect the success of shade matching. This study aimed to compare these two methods and evaluate the effect of experience and gender on the results. Three volunteers' maxillary central incisor teeth were evaluated using (DSM) and (ISM) methods by 87 examiners (42 males, 45 females). These examiners were further divided into three groups based on their clinical experience: Undergraduate Preclinical Dental Students (UPDS) with 31 examiners, Undergraduate Clinical Dental Students (UCDS) with 34 examiners, and Postgraduate Dental Students from the Department of Prosthodontics (PDS) with 22 examiners. The spectrophotometer device results of three teeth were considered as a reference for shade matching. Statistical analyses of the data were performed using Kruskal-Wallis, Mann-Whitney U, and Chi-square tests. No significant difference was found between indirect and direct methods according to Perfect Matches (p > 0.05). However, according to Shade Matching Deviation Score (SMDS) values a statistically significant difference was found between the two methods where the best result was obtained with the ISM method (p < 0.05). There was a significant difference between the PDS group and the other two groups in terms of clinical experience (p < 0.05). There was no significant difference between gender groups (p > 0.05). Digital images, captured under standardized lighting conditions, may serve as a reliable alternative method for direct shade matching. The (ISM) method requires a camera, related accessories, and computer skills. However, as these tools are commonly available nowadays, the focus for practitioners should be on effectively learning and applying these tools to achieve the best results. While clinical experience plays a significant role in the shade matching process, gender does not appear to have a substantial influence. This study found no significant differences between the (DSM) and (ISM) methods, leaving the clinical relevance of this method open to debate. However, the ISM method yielded superior responses. Despite requiring specialized tools, conditions, and training, the widespread use of cameras and computers in modern clinics makes the necessary equipment and software readily available. This method enhances clinician-technician communication, potentially improving prosthesis esthetics and patient satisfaction, especially for less experienced clinicians or those with color deficiencies. Further research is crucial to determine its clinical significance.