Trendsetter: John F. Kennedy 

While we're blogging, taking pictures, and getting drunk in overpriced bars with other dudes whilst rocking our cropped pants and bright socks, you know what John F. Kennedy was doing? Sailing on a yacht, having extra marital affairs with Marilyn Monroe, and leading the free world. As one of the greatest style icons who ever did it, J.F.K. made his look, especially this one, seem effortless. Isn't that the real key to style? Looking effortless in cropped pants with bright socks and trying to get with chicks like Marilyn Monroe?