Lest you are a male offspring of one Marcus Mumford, or perhaps even the Wimbledonian himself, wearing a newsboy cap makes you look like king effboi of the west with a strong affinity for Elliott Smith and pickled whiskey. I think newsboy caps were actually collectively scoffed at during the “newsboy era,” which according to the Disney movie Newsies was around the turn of the 19th century. You think Yung Cowboy actually liked wearing that stupid hat? Damn Joseph Pulitzer and the New York World bricking the 1899 workwear alphet game.