Sam Edelman Penny Leather Riding Boots in whisky leather, women’s 4M (euro 33.5)

This classic leather riding boot, Penny, adds luxe equestrian chic to any outfit with its sleek, timeless silhouette. This universally-flattering style features a pull-on tab and back zipper closure for comfort and ease. Pair them with skinny jeans and a blazer now or bare legs and a tailored dress later for unstudied preppy elegance. Some peeling on upper inside. See photos. Retail for $200