In this study, six mainland Chinese designer brands—Xander Zhou, Sankuanz, Sean Suen, Feng Chen Wang, Pronounce, and Angel Chen—were selected that had their works presented at both Chinese and global fashion shows between 2016 and 2021. By analyzing the design characteristics of each brand, it is possible to understand the style characteristics and trends of Chinese menswear designs. A case study approach was adopted utilizing literature data, whereby 1663 photos were collected from the fashion information website POP (www.pop-fashion.com). Changes in Chinese men's image and the menswear market were identified. The design characteristics of modern Chinese menswear are as follows. First, the results from analyzing the target brands show that each brand has a distinct personality. Compared with the traditional or formal style, urban casual and sports styles (based on street style) account for a larger proportion. Second, the boundaries between different styles are becoming ambiguous, and contrasting styles are harmoniously expressed by breaking down boundaries through changes and combinations of colors, materials, and details. Third, after examining the overall trend, 2018 was a watershed point, after which the design trend has changed from either conservative or exaggerated to a practical and everyday style, demonstrating a genderless trend.