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. With socks, without socks, sometimes even with white tube socks and shorts, the penny loafer became a centerpiece of the newly solidifying post-war “Ivy Look.” By this time a phone call cost ten cents, some fiscally responsible young gentleman made the switch from pennies to dimes. But, as is often the case with the preppy set, some held onto the traditional penny, or maybe they never even noticed the change in price.

Talented singers, teenagers and Wall Street workes fit the same shoes with the same coins!