The fashion industry is an integral part of people’s lives with different purchasing behaviors depending on age and education. In this paper, we focused on the perception of online shopping for second-hand clothes and shoes among Generation Z. This group has a lot of experience in using technology, so online shopping is a suitable way to buy second-hand clothes. The article aims to analyze the online shopping behavior of Gen Z, focusing on benefits, obstacles, environmental awareness, and preferred shopping platforms. We studied consumer preferences in shopping for second-hand clothes based on a sample consisting of 340 respondents representing Generation Z through an online Google Forms questionnaire published from November to January. The results show that price is the biggest advantage of shopping for second-hand clothes. Moreover, we found that the environmental aspect plays a significant role for all consumers, regardless of the online experience of shopping for second-hand clothes and shoes. The correspondence maps demonstrate that consumers with shopping experience planning a future purchase of second-hand clothing are aware of the environmental impact of purchasing clothing together with potential buyers of second-hand clothing, unlike consumers without any interest in purchasing second-hand clothing. These consumers and potential buyers of second-hand clothing consider environmental protection and high-quality, diverse (unique) clothing to be key benefits, in contrast to a smaller selection and used clothing. These conclusions provide a theoretical basis for understanding the sustainability and shopping requirements of the selected group.