Scrolling through hundreds of street style photos will never get boring. Why? Because each season, and really, each city, has such a distinct aesthetic. New York keeps things cool and casual — hoodies with pleated skirts, tulle dresses with beat-up sneakers, a satin blouse with some high-waisted mom jeans. London , too, knows how to mix the high-low: Topshop with J.W. Anderson, H&M with Rejina Pyo, Zara with Erdem. It's all about balance. But when it comes to Milan, well, there's no sweatpants in sight. That's right: In Italy, they're not afraid to get fancy.