With his numerous works, the well-known prolific American expatriate novelist and essayist, Henry James considerably contributed to enriching our perception of the transition process in the USA to modernism as an author witnessing both late nineteenth and early twentieth centuries. After experiencing a long period of puritanical order and remaining stuck in the strictly established moral rules, American New England society was breaking its earlier conservative crust with the advent of the new century. James shed light on this transition process with many of his works such as The Ambassadors, Bostonians and Transatlantic Sketches. In this study, The Ambassadors, which can be seen as the projection of James's European experiences, is scrutinized with respect to the comparative representations of Paris and Woollett, and in a bigger scope, Europe and America. Spending most of his time by commuting between the Old and New World, James provided his readers with unique perspectives about these places in hereby-handled fiction through the eye of his protagonist, Strether. Drawing on the distinctions made between Woollett and Paris, this article examines how James reconstructs modern American identity hinging upon the two sides of Atlantic.