More comfortable, more durable, cheaper, better selection of comfortable footwear that doesn't need servicing by a person at the airport or the main floor of an office building... need I go on?
If you pay $300 for well constructed leather boots, they will last you for years, even if you wear them almost every day. They are also much more easily repaired than sneakers, which gives you another nine months of life. So proper boots are actually a better investment than sneakers.
I was really skeptical until I bought really nice boots from Fluevog. Additionally, a good company will stand behind their boots, and give a warranty. Fluevog replaced my boots for free because there was a manufacturing error in the first pair.
Try it. Every man deserves a decent pair of boots. They provide great support and feel amazing.