But seriously, perhaps the most frustrating part of this conversation is the debate on what constitutes a heel or not. If three inches is too far, then are two inches the new one-inch? They're just shoes. And they contain a pretty cool, wild history , just as most iconic wardrobe staples do. A direct descendant of the flamenco boot, the Cuban-heeled Chelsea boot has survived and evolved an endless cycle of trends and their decades: the Beatles era of the '60s, the punk movement of the late '80s and early '90s, and now, the pointed-toe craze that's strutting across the runways, from New York to Milan. By arguing whether or not a heeled boot falls under the heel umbrella at all, we forget how cool it is the boot is still being worn, especially by such a mainstream, "hunky" heartthrob as Styles.