The newsboy cap started off as the flat cap, which was created in 1571 after Parliament imposed a law in Northern England that required all males over the age of six to wear woolen hats every Sunday and holiday – anyone who did not was subject to a fine. The law was established in an attempt to bolster the wool industry. However, it was only enforced among the working class. Still, the style grew popular among working-class men, and when the law was abolished 30 years later, working-class men and boys continued to wear their flat caps. Over time, the style evolved and became associated with certain trades. The newsboy cap directly evolved from the flat cap, but featured a rounder and puffier design that almost always included a button on the top. In the 1800s, the style became more widely popular. (It was even famously worn by the violent Peaky Blinders gang in the 1890s – a far cry from its newsboy origins.) By the 1920s, the newsboy cap had made its way into upper-class wardrobes, although wealthy wearers often purchased expensive tweed versions rather than hats made from wool. Today, the newsboy cap remains a popular hat style that carries its history with it: It is at once classic and rebellious, while the many affordable versions pay homage to the hat’s working-class roots.