Trendsetter: Bing Crosby

When Levi Strauss came to San Francisco all the way from Bavaria to tailor men's workpants out of denim, we have a feeling he didn't think they would become this big. Even though denim did make its way to Western wear in the 1930s with John Wayne and fellow on-screen cowboys riding into the sunset with them on, it took singer Bing Crosby to take them out of that cowboy-wear mentality. As one of the most influential musicians ever with more #1 hits than Elvis and the Beatles, Bing Crosby made dry denim more than just what you'd see on a cowboy, especially as he wore his custom-Levis denim tuxedo with pride.