Oversized fashion is again in the spotlight due to the influence of retro fashion. This has created new fashion trends with methods different from those of the past. This analysis examines recent trends by sorting these looks according to new and different methods of judging their appearance. A new categorization of the oversized look and its configurations has been created, one which separates “big” looks, partial changes, and layered looks. This research was based on historical review and previous studies. Three thousand one hundred thirty-six photos of oversized looks that have appeared in collections over the past five years were gathered, and their appearance was categorized according to type. The categorization results showed that big looks (55.1%) were most prevalent, followed by partial alterations (36.35%), and layered looks (8.45%). In comparison to prior oversized clothing production, new permutations of the “Big” look expanded the silhouettes of torso, shoulders, neckline and collar. Partial changes have expanded from the broadened shoulders of the 1980s. Today these styles expand the shoulders and armholes vertically or horizontally, which dramatically exaggerates the sleeves and collar. The layered look no longer simply features overlapping layers but takes the form of over-layering through cuts and insertions. Through such analysis it is clear that modern oversized looks break away from the simple expanded forms and production methods of the past. They now attempt to realize an exaggerated beauty of form regarding each clothing component and also maximize decorative effects through innovative drafting or sewing methods.