Boomers Said: “A Penny for Your Shoes”

Mister Boomer needs a new pair of shoes. He hasn’t had much luck in his search. Cost notwithstanding, the “modern” styles of angular side cuts, futuristic heels and crazy toe shapes aren’t conducive to this stage in life. Nonetheless, sitting among the rows of “footwear systems” (as opposed to “shoes”), sat a familiar sight: a penny loafer.

The history of the penny loafer in the U.S. dates back a few decades before the boomer era. It was the 1930s when the “loafer” was invented for the American market. After Esquire magazine produced a photo shoot of Norwegian farmers, standing with their dairy cows, in what was known as a “loaf” area before the cows were milked, footwear gurus found inspiration. Some say this style of slip-on shoe was originally inspired by shoes worn by Norwegian fisherman rather than farmers, but it appears the Esquire photo layout is what caught the attention of G.H. Bass, a boot maker who’s factory was in Wilton, Maine. In 1934 Bass developed and sold a slip-on shoe — a loafer — styled after those worn by Norwegians. He called his loafer a Weejun to reflect this influence. The footwear designers added a strip of leather across the tongue of the shoe, with a small cutout in it. Legend has it the shape of the original opening was a reminder of an open mouth during a kiss. Mr. Bass’s wife kissed her husband on the cheek each morning as he strode off to work.

The penny loafer became a big deal for early boomers when Ivy League students began wearing them with their khakis. Adopted by “prep school” students, the loafers became a part of the “preppie” style of dress. Some students slipped pennies into the slots of the shoes as their own personal fashion statement, and the “penny loafer” was born. Legend has it placing a “lucky penny” in a shoe was derived from the practice of putting a penny in a bride’s shoe on her wedding day to give the couple good luck and wealth.

Others noticed the slot could easily hold a dime, which happened to be the cost of a pay phone call at the time. Dimes placed into the slot of each shoe meant that you’d always have money for a phone call if the need should ever arise. The craze — whether worn with pennies, nickels or dimes inserted into the shoe’s slots — was immensely popular until the sneaker started making inroads into the footwear of the 1960s. Still, the penny loafer remained a staple among dress footwear, for both men and women, but especially for men. It fell slightly out of favor in the late 1970s and ’80s for non-preppies, but appears to have have made a comeback as a timeless classic.

Mister Boomer’s brother owned a pair in his high school days. Mister B, however, can’t recall ever owning a pair of penny loafers before his college days. When the heels of his blue suede saddle shoes finally gave out, he purchased a pair of vinyl penny loafers that he wore the rest of his college days when sneakers were impractical, such as in winter weather.

Somewhere in the late 1990s, Mister B bought a pair of leather penny loafers for work. The shoes lasted for years, and when the heels gave way, he had new ones put on. Once the soles gave out, the shoes were retired. Now he’s wondering, is it time for a new pair?

What do you think of penny loafers, boomers? Are they timeless classics or relics of a time long passed?