Why I love them: Riding boots allow you to look like the epitome of equestrian chic, even if you've never been on a horse in your life. They're comfortable, easy to get into, and have a simple, classic silhouette. How to wear them: Riding boots are, of course, made to be worn with slim-fitting tailored pieces — opt for a pair of dark-wash skinny jeans or trousers, then go a bit fuller on top, like with a printed blouse or slouchy tee. For the ultimate in polo-cool, add a fitted blazer with elbow patches. Shop the runway: Gucci Trish High-Heel Riding Boots