The process of aging population is increasing the relevance of comprehending age-related changes in skin structure and function, as well as their implications for clinical care. This narrative review explores aspects of the intrinsic and extrinsic mechanisms of skin aging, their molecular and morphological consequences, and their clinical expression, with particular attention to chronic cutaneous insufficiency. The intrinsic aging process is reflecting declining cellular functionality, impaired tissue homeostasis, and endocrine changes, especially regarding estrogen deficiency after menopause. These processes are reducing collagen synthesis, hydration, and elasticity and thus contributing to epidermal and dermal atrophy and barrier dysfunction. On the other hand, extrinsic aging is driven mainly by cumulative ultraviolet exposure, with additional contributions from pollution, smoking, diet, and behavioral and psychosocial factors. Processes such as oxidative stress, inflammation, DNA damage, glycation, and increased matrix metalloproteinase activity promote extracellular matrix degradation, linking the environmental exposure to the photoaging and cutaneous carcinogenesis. Main clinical manifestations include xerosis, chronic pruritus, pigmentary changes, benign lesions, actinic keratoses, and basal cell and squamous cell carcinomas. Inflammatory, allergic, autoimmune, and drug-induced dermatoses, including psoriasis, lichen planus, and bullous pemphigoid, are complicating healthcare in older adults, while systemic comorbidities and medication use are influencing clinical presentation and treatment. Dermatoporosis is characterized by cutaneous atrophy, purpura, pseudoscars, and susceptibility to injury after minor trauma. Reduced hyaluronic acid availability and CD44 expression contribute to impaired hydration and mechanical resilience, potentially leading to ulceration and deep dissecting hematomas. Management measures are emphasizing the role of photoprotection, skin hydration, trauma prevention, and reduction of modifiable exposures, with corticosteroid use warranting reassessment in secondary dermatoporosis. Other discussed approaches are topical hyaluronic acid, retinoids, alpha-hydroxy acids, and vitamin C, but the proposed interventions have limited supporting evidence. Therefore, it is considered that early recognition of these interconnected changes may be supportive for planning prevention, a timely diagnosis, and individualized care, based on considerations like skin fragility, associated disease, and treatment burden in older patients.