7. Ankle Bootie The perfect addition to a weekend wardrobe, the ankle bootie looks both pulled together and casual at the same time. And the bootie is actually comfortable. The next time you want to slip on your ballet flats or a pair of sneakers, try mixing it up with a chic ankle bootie to give your outfit a little boost without sacrificing comfort. And PS: They take up much less room in your closet, which means, yup, more room for MORE SHOES!