Those Retired Running Shoes — Your old running shoes served you well on the track, but even though they're not fit for serious pavement pounding anymore, they're still shoes. Keep the casual thing going, but choose pieces that are a little more elevated: Think printed jeans, a beautifully draped tee, and an army coat with some structure. Top it off with a necklace — no sweat!

Clockwise from top left: AE Floral Legging, $39.99, available at American Eagle; Reiss Della Mesh Trim T-Shirt, $26, available at Reiss; H&M Arrow Necklace, $14.95, available at H&M; rag & bone Wynn Coat, $895, available at rag & bone; Meredith Wendell Small Green Eye Handbag, $290, available at Meredith Wendell.