The penny loafer is a classic. It’s every boy’s first dress shoe (no laces), looks perfect beaten-up and broken down through your college days, and later is formal enough for the office. It’s a lifelong wardrobe staple and all in all just about the most versatile shoe you will ever slip on. But: why the penny? Your Two Cents’ Worth Back in the 1930s, the pay phone in the phone booth cost a paltry two cents.  The new loafer design allowed just enough space for a penny in each shoe, equaling the cost of an emergency phone call. Thus, the penny and the loafer were united. Everything Old Is New Again The penny loafer had its heyday in the late 1950s and early ’60s.