There are very few hard and fast rules in fashion, but if you only remember one thing, remember this: Thou shalt not wear square-toed shoes. Why square-toed shoes have had more staying power than lesser sins (think: acid wash jeans) is impossible to figure out. Instead of dwelling on their puzzling refusal to disappear, we asked some heavy hitters to make the case for keeping our ten round pegs off square soles. David Nau of Sperry Top-Sider, Rem D. Koolhaas from United Nude, and Doug Jakubowski of Perry Ellis all told us to consider current trends and the roundness of our legs.

It all comes down to shape and size. Ever since the heyday of loose-fitting pants in the 1920s, men's pants have gotten progressively more tailored, more tapered, and more fitted. Today's pants make square-toed shoes look like flippers. Even Koolhaas, usually one to push the envelope, says this is one trend he's happy to watch die: "I remember my first and only pair… a pair of cowboy boots, similar to the ones that Clint Eastwood wears in 'The Good the Bad and the Ugly.' I even had a poncho sweater to go with it. This was a cool look back then, but I would laugh at myself for wearing them now.... They don't follow the body and they don't follow the function." Sounds like that was one hell of an outfit.

"Although they may have been worn by the Puritans... classic prep and American heritage looks are in right now and square-toed shoes are anything but preppy, "says David Nau, VP of Men's Design at Sperry Top-Sider. Nau added that certain types of shoes don't seem to go with any look, but stand apart.

The thing is, most square-toed types are embracing convenience, not chasing a "look." Many square-toed shoes are convenient slip-ons, but that same convenience can be achieved with a stylish loafer. If ease of wear is something you're looking for, buy some serious-minded driving shoes. They may look good with almost everything and come across as playful rather than ill-considered.

Or just stick with a shoe with rounded shape. Whether you're looking for something to go with a suit for work or with jeans for downtime, Doug Jakubowski, Chief Merchandising Officer at Perry Ellis, suggests a slimmer, updated style such as the saddle shoe or wingtip. They don't slide on as easily, but boy do they look better than those boxy clunkers.