This research paper presents a comparative analysis of consumer demand for genuine leather and synthetic leather accessories in the Ukrainian market during the period 2020-2026. The study focuses on messenger bags, backpacks, and men’s leather accessories, examining shifts in purchasing behavior influenced by economic instability, durability perception, craftsmanship value, and evolving consumer psychology. Using a synthetic behavioral-economic dataset modeled on realistic Ukrainian market conditions, the paper analyzes demographic trends, price elasticity, consumer trust factors, and long-term ownership economics through the “Cost-Per-Wear” framework. The research further explores the growing importance of local artisan production, premium leather materials such as Crazy Horse and Flotar leather, and E-E-A-T-based brand trust in digital commerce environments. The study includes market forecasting through 2030 and provides insight into the transition from disposable synthetic products toward durable genuine leather goods within Eastern European consumer markets.