Grant Canoe Penny

They say jet-setting Europeans were the first to wear them as street shoes, pioneering the trend in summertime St. Tropez. By the 1960s, the look had caught on everywhere, making them a warm weather favorite on every continent. Ours are crafted using a traditional moccasin construction—a time-tested technique that started in New England. This method ensures that the exceptionally plush leather wraps around the entire foot, cradling it for a sock-like fit. Drivers generally feature one of two kinds of soles. The more traditional styles are nubbed (also called punch-through because of the way the nubs come through the leather outsole); these are more flexible and have a barefoot feel. The second type, called a unit outsole, is more substantial, and built from a single piece of rubber.