If you hear the word "leggings" and still think athleisure, trust us, these are not your average Lululemons . And if you're already sold on the value and wardrobe-expanding potential of a solid leather legging (real or faux!) but aren't sure what to wear it with, that's totally OK. No one actually comes out looking like Sandy 2.0 in Grease on their first try. Ahead, we've compiled a range of tips and outfit ideas taken directly from the street style champions themselves to guide you through the execution of this trend. We've even ranked each look on a scale of simple to surprising so you can push the boundaries of your wardrobe with each wear.