Wingtips. . . in sneaker form? Pure genius! These high-cut leather sneakers from Swear Iggy at Ssense have a dress-shoe effect with paneling, except that with these ones, you’re getting a softer sole, a more jeans-friendly shape, and an overall seasonless effect that works wonders on the most boring of outfits. Bubble ribbing at the ankles means cushy comfort with minimal effort. Sizes 40-45. [$245 at ssense]