This study analyzed how the elements of dress from ancient to modern times have been reinterpreted in a contemporary manner and reflected in the designs of Dolce and Gabbana’s collections. Both theoretical research and case studies were used. For the theoretical research, the literature related to fashion and retro, previous studies, and internet sources were examined. The case studies focused on analyses from Vogue Runway, the official Dolce and Gabbana website, and Runway Magazine. The analysis showed that in Dolce and Gabbana’s collections, retro tendencies were highlighted using the characteristic clothing forms and architectural prints of ancient Greece. The use of soft materials like chitons and himations naturally revealed the body lines, expressing the beauty of the human form from antiquity. In the medieval period, retro styles were expressed through accessories and medieval-style prints, while Christian symbolic decorations conveyed the influence of medieval religious themes. In the ancient and medieval periods, print-centric visual elements were prominent, whereas the reinterpretations of dress based on form were more pronounced in the Renaissance and modern periods. In the Renaissance, men’s clothing items were reinterpreted for women’s fashion, and decorative elements were used to express retro and aristocratic tendencies. The Empire style of the modern era showcased a natural silhouette influenced by neoclassicism, while the Romantic era emphasized femininity in its styles, reinterpreting crinolines as outer garments. In conclusion, retro styles, which reinterpret historical dress, have been utilized continuously in Dolce and Gabbana’s collections.