2011. With a special appearance in his beloved Toronto for the 2011 JUNO Awards, Drake took a bit of a more serious approach. The look, seemingly fit for a young advertising exec, brought on a more refined image for the rapper. This look stands as a defining moment in Drake’s style evolution. Like his trend-setting predecessor Kanye West, Drake has always been able to ‘fit in’ by purposefully not fitting in; defining his own personal style despite the heavily cliched look sported by most Hip Hop / Rap Artists.