History of Fashion: The Penny Loafer

by Jessica Barr

Penny Loafers, uncomfortable as they ordinarily may be, have had and will always have a special place in my heart. Autumn is the season for loafers and bulky sweaters paired with chiffon shorts.

It wasn’t until my freshman year of college that I fell in love with loafers as the fall staple, yet here I am wearing the same two pairs I purchased pre-Trump era.

Like everything in life, the penny loafer has evolved to meet the needs of the modern individual; with a shoe originally crafted for comfort (ironic, I know), how much farther can we really go? So when, where and how did the shoes begin their journey to what they are now–my favorite white patent leather pair with a studded vamp?

Our beloved loafers first came to life in the late 1930s, not only modeled after the shoes worn by Norweigan fishermen, but inspired by their name as well. G.H Bass was the foremost creator of the new shoe, The Weejun. Loafers, made for comfort and durability, were essentially leather moccasins at their start in the pre-sneaker era. From the ’40s to the ’60s, until counterculture shoes gained popularity, penny loafers found their niche on college campuses with “preppy” style.

The name “penny loafer” came from what research has proved to be a whopping compilation of rumors. Some say girls would keep a penny in the vamp when going on first dates in order to afford a rescue payphone call. Since we aren’t sure if phone calls ever cost just a penny, the theory seems fabricated.

Despite the countless rumors that come with wondering why it was in fashion to stick a penny in the shaft of the vamp, we know some way, somehow, there is truth behind the trend that coined the name of the penny loafer.

After infiltrating the Ivy League, the loafer went high fashion in 1953 when Gucci brought his Italian style to New York. Coming stateside beforehand, Aldo Gucci took inspiration from the Weejun and went back to Italy with plans to recreate the design. After sketching the first-ever high fashion loafer, Gucci replaced the penny bit with a horsebit and changed their classic color from brown to black. Thus, we have the beginning of the penny loafer as a wardrobe staple.


A version of this post originally appeared in “Tenacity” The Teller October 2019 Issue #7

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