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The purpose of this study is to analyze the granny look of the new-tro trend via Alessandro Michele’s Gucci collection and to provide a reference standard for future design developments by identifying the representation of the granny look. To analyze the new-tro trend and the granny look, basic concepts were analyzed through aesthetic and art books and the photographic data were collected through Internet sites. A total of 186 fashion images were considered as granny look by five clothing experts. The images were subdivided into silhouettes and items, materials, patterns, and colors to analyze the modeling factors and identify the intrinsic inner meaning based on the theory of Nostalgia. The analysis showed that the silhouette was expressed naturally without exaggeration or shrinkage. The thermosetting materials included fur, velvet, knit and quilted materials, while the colors showed raw and faded shades based on the use of natural colors. The patterns were mostly natural, such as flowers, leaves, and stalks, which were aimed at nature. The inner meaning of the granny look is based on the theory of Nostalgia, primarily because it is an emotional fairy tale and second, it reflected the sessions of nature. Also, it is a reinterpretation of the narrative. In conclusion, the academic and fashion industries need to understand the various emerging trends in accordance with the social and cultural backgrounds to derive a positive benefit.