SANTONI

Simon leather penny loafer

As it has been hand-making shoes since 1975, it's safe to say Italian luxury label Santoni knows a thing or two about quality, construction and fine leather (that all-important footwear trifecta). Impeccably crafted, the Simon loafer features the cross-front strap with the classic window for a penny (you'll need to supply your own, however) and is shaped into an almond-toe silhouette. Team with cords, chinos and weekend wools for the native Milanese look.