Black leather loafers with a rounded square toe and that high-cut vamp The Row does so well. Mary-Kate and Ashley Olsen founded the brand in 2006 with Savile Row tailoring in mind, and you can tell they care about the details most people skip. The stacked heel gives you just enough height to feel polished without making you think about your feet all day. Made in Italy from matte calfskin that gets better as it ages.