For days when running shoes are too casual, and Chelsea boots are too dressy, a leather tennis shoe is the perfect middle ground. These Cole Haan favorites are made of burnished, hand-stained leather and have a classic silhouette that looks expensive and elegant. Pair them with anything from jeans to a suit and they won't look out of place. These come in two widths (medium and wide) in sizes 7 to 16. Don't miss the warm brown and clean white options, also on sale.
"[They] effortlessly transition from office to weekend wear," one stylish shopper said. "They're incredibly comfortable, stylish and versatile, pairing perfectly with both blazers and trousers for a polished work look, or with jeans for a laid-back weekend vibe."