Nike Roshe Run
Buy It Now at Nike Store, $70

In case you haven't heard, the Nike Roshe Run is like, the shoe of the summer y'all. But lightweight running shoes have definitely broken out of performance gear and onto the feet of stylish dudes everywhere. Why? Well, they've finally managed to balance out technical aspects like breathability and lightweight materials with designs and colorways that make them look like shoes meant to be worn and not machines for your feet made to make you less fat. It's a win-win.