Why I love them: Quite possibly the easiest and most flattering boot style out there, ankle boots add a polished, fun look without taking away from the rest of your ensemble. Whether you choose a sky-high heel or no heel at all, they work seamlessly into your wardrobe and elongate your legs like no other. How to wear them: With ankle booties, the possibilities are endless. Flat, desert-style boots are perfect with skirts, shorts and flirty dresses, while high-heeled styles can dress up almost anything. You name it, ankle booties will look great with it. Shop the runway:DKNY Mary Oxford Bootie