Wearing a dress over pants is one of those things fashion girls do that I feel like I could never pull off. But it’s actually pretty practical — it looks chic, keeps your legs warmer than tights (minus the risk of runs), gives dresses that cool tomboy contrast, and extends your wardrobe by essentially turning a dress into a top or jacket. The key to making it working is sticking to tailored silhouettes—a shift dress over tailored trousers, or an A-line skirt over skinnies. You don’t want to look bulky or lumpy. But from there you basically treat the shirt like a dress and just pull on your pants. Still sound confusing? Yeah, I agree. I find a picture is worth a thousand words, so I just like to copy these cool examples of how to wear a dress over pants.