Background: Hypertrophic scars and keloids can be described as variations of typical wound healing. Aim of this study was to find out the dermoscopic differentiating features between keloids and hypertrophic scars in their recent phases of development in Egyptian population. Patients and Methods: An observational cross-sectional design of 30 cases that assigned according to histopathological analysis into two groups; Keloids and Hypertrophic scars. Then the polarized non-contact mode of a Dermlite© DL3 “Gen, USA" at a magnification of 10 × was used to capture dermoscopic images for both groups. The surface morphology and the dermoscopic criteria were recorded directly from the patients and included vascular structures (Arborizing, linear and comma shaped vessels), erythematous or white patches. Results: Statistical analysis revealed that patients with keloids are more likely to be associated with the presence vascular structures on dermatoscopy. The analysis of types of vascular structures showed that arborizing vessels, in particular, were significantly related to keloids. In contrast, the dominant dermoscopic feature in Hypertrophic scarring was the presence of scarring as presented in the form of erythematous or white patches with scanty or absent vascularization. Conclusions: Dermatoscopy should be considered as a routine investigation of any case with abnormal scarring for a better differentiation between keloids and hypertrophic scars, and hence a better evaluation and treatment of each type.