Raf Simons ($291), rafsimons.com
Running shoes are the most comfortable footwear around, yet for the past decade or so most of us have felt uncomfortable being seen in them. Fortunately, it's once again acceptable—even sanctioned—to wear them outside the gym. You can thank guys like Stefano Pilati, creative director of Yves Saint Laurent, who regularly kicks it in New Balance when he's out on the town, and designer Raf Simons, who created a pair of sneakers for the runway that you can actually run in.
Nike ($90), nike.com