Fashion photography is a form of art. Several important photographers are challenging themselves to work and be creative and innovative to make an impact on the Fashion Industry. Creativity and originality of style are key elements to affirm themselves in an increasingly crowded and competitive world of advertising photography. Some photographers challenge conventions to assert their innovative ideas. This article examines how two of the most important fashion photographers Oliviero Toscani Italian, and David La Chapelle American, marked an era in advertising photography using similar content but with totally different technique and style. There are many similarities in the two photographers work, but a big difference in the implementation and execution of the photographic project. The following article aims to highlight resemblances and differences between two artists considered among the most important and influential photographers of the 20th century