Film: The Great Gatsby
Year: 2013
Signature Look: The Original New York City Cool Guy

Jay Gatsby predates what Ralph Lauren became. In the same way fashion transformed Ralph Lifschitz to Ralph Lauren, Gatsby uses wealth and style to become his own version of the American Dream. His personal style exhibits his nouveau riche luxe attitude and lifestyle, only wanting the best of the best, whether it came to shirts, cars, or suits. It's no surprise that Brooks Brothers took the helm of the beautifully-crafted menswear in the film, poring through their own archives for the costumes. Author F. Scott Fitzgerald even wore the brand himself. Gatsby's evolution from midwestern farmboy to self-made millionaire is a very hip-hop story that encapsulates just how clothes can really make the man.