As environmental concerns continue to rise, the design industry is shifting its focus towards sustainable products and adopting circular economy principles. Design students are similarly incorporating this focus into their school projects. However, the selection of sustainable strategies often neglects or compromises user experience, as these strategies do not directly correlate with how users interact with and perceive the products. This oversight can lead to difficulties in the initial design stages and even potential market rejection if a product, while sustainable, fails to deliver a satisfactory user experience. Hence, this study aims to explore the link between product types, sustainable design strategies—biodegradability, longevity, servitization, and upcycling—and user experience, focusing on the degree of user body contact. Then, 31 participants underwent a one-week trial, experiencing various sustainable strategies applied to 16 intimate or non-intimate products. The user experience was assessed based on utility, attractiveness, and green awareness. Feedback was collected through online surveys and open-ended interviews. Both quantitative and qualitative data were used to summarize the relationship between product intimacy, sustainable design strategies, and user experience. Results revealed that no specific circular design strategy significantly influenced user experience for both intimate and non-intimate products. However, non-intimate products generally received better user feedback compared to intimate ones. Interviews suggested this preference may be due to users’ strong attachment to familiar products, emphasizing the need for new products to significantly outperform existing ones to garner positive reception. Overall, this study contributes to comprehension of user experience and developing of sustainable products.