I don't know, considering Sam Lucchesee reated a square toe design specifically for John Wayne.....I figure he was fine with square toes.
"Peck wasn’t the only familiar face to call on Lucchese, either. In October 1951, a tall man blew through the door into Lucchese’s shop and requested a pair of boots with a distinctive square toe. But this man was more popular than Peck, at least at the time. Though he’d been cast in small roles since the 1920s, his career had really taken off two years earlier, with a starring role in war film that had earned him an Academy Award nomination.
The man, of course, was John Wayne, and he was at the start of his career as an All-American Western hero. So naturally, he needed a pair of cowboy boots.
The square toe on his boots became known as the famous – and controversial – “John Wayne Toe,” and like Peck, Wayne became a frequent customer and proponent of Lucchese. In fact, several of his style of boots – notably goat and alligator leather – can be found on the Lucchese website. "