There is a reason the penny loafer has remained a subculture and smart-casual staple for decades. Sebago does it properly with the Classic Dan, featuring a corrected grain leather upper that gives off a clean, polished sheen right out of the box. The handsewn construction and beefroll stitching on the sides show off the brand's heritage without shouting about it. These are built with a molded rubber heel and a treated leather sole, meaning they need a little breaking in but will mold to your feet beautifully over time. Slip them on with white socks and cropped trousers for that classic Ivy League look, or keep things simple with some dark wash denim. They are sturdy, unpretentious, and look better the more you wear them.