Assessment of the impact of hypertension on the involutive changes in facial skin is a topical issue due to high prevalence of this pathology. Thus, about 40% of adult population of the Russian Federation have high blood pressure. Along with this, the number of middle-aged females who seek advice of cosmetologists and plastic surgeons increases over time. This dictates the need to take into account possible risks of postoperative complications in the skin. We report the results of morphological studies of facial skin of middle-aged females with stage I—II arterial hypertension (AH) and highlight the complex of morphological criteria for the assessment of involutive changes. The impact of AH on the quantitative and qualitative characteristics of the epidermis, dermis, and dermal arterioles is shown. Comparative analysis of skin morphology has shown that epidermal thickness in hypertensive patients tends to increase, while the thickness of the stratum corneum tends to decrease. Significant thickening and smoothing of the basal membrane was also observed. Significant increase in the amount of elastic fibers and their uneven distribution was visualized in the dermis. Hypertensive patients demonstrated significant increase in the external and internal diameters of dermal arterioles, statistically significant increase in arteriolar wall thickness, and significant increase in Kernohan Index.