We all have leggings in our closets, and while they're comfortable and sporty, making them sophisticated and fashion-forward can be tricky. With cooler months upon us, we're going to show you three fresh ways to wear your favorite pair of leggings this season. From classic cotton, to leather, to cute capris, watch how we make leggings look cool. On Allison: Rebecca Taylor top, American Apparel leggings, Sam Edleman booties, Lia Sophia bracelets. Model: Chloe, Vision Model Management.