A Guide to Chukka Boots
December 1, 2024
The penny loafer has been a timeless essential for generations, revered for its versatility and unshakeable popularity. Able to elevate the most laidback looks or serve as the perfect finishing touch to smart casual ones. Whether you pair them with tapered trousers or linen shorts, penny loafers always make a chic statement.
Nils Tveranger was a Norwegian man who, in the early 1900s, wanted to give the teser – a traditional laceless shoe worn by local fishermen and peasants – an upgrade. The teser was made from leather, making it both tough and lightweight. After studying cordwaining in America, Tveranger came back to Norway and combined elements of the teser and Iroquois Native Americans’ moccasins to create the Aurland moccasin.
The Aurland moccasin first caught the eye of European and American travelers during the interwar period. Rumors of exceptional salmon fishing and mountaineering in the Valley of Aurland, Bergen drew them in, and they quickly noticed the comfortable-looking footwear worn by local fishermen. They were amazed by the simplicity of the shoe and took home a pair or two as souvenirs. These fashionable foreigners — wealthy sportsmen and the well-traveled elite — wore Aurland shoes back home in stylish places like Palm Beach. In 1935, an Esquire magazine staffer was the first to spot them there. According to Esquire, Aurland shoes were usually paired with light-colored suits, a Panama hat, or a fedora.
The Aurland moccasin caught the eye of Arnold Gigrich, founder of Esquire, who saw its potential. He partnered with a distributor to bring a sample to John Bass, son of the founder of American footwear label G.H. Bass. By 1936, the label had adapted the Aurland into the Weejun: a thicker-soled adaptation with a distinctive cutout in the middle of the strap. The Weejun quickly became known for its style and comfort, and remains a popular choice among discerning shoppers today.
The Weejun—an American take on the word “Norwegian”—was advertised as Norwegian fishing shoes and first retailed for $6.50. An early advertisement refers to the penny loafer’s versatility: “Not shoes, not slippers, not moccasins, they are ideal for the beach, a camping trip, or lounging about the locker room or house. Fine for informal occasions.” A later advertisement aptly calls the penny loafer the “Symbol of Elegant Leisure.” Penny loafers became an instant hit, so much so that women even began buying them for themselves and brands around the country began producing their take on the style. Today, penny loafers are still a popular choice for those seeking a stylish yet comfortable shoe option.
The penny loafer’s convenient laceless design, well-priced and ideal for rushing to class in the mornings, made it the ubiquitous shoe for American schools and college campuses from the 1940s to the late 1960s. Worn by students year-round and paired with everything from shorts to tweed separates, the term “penny loafer” was widely used as the go-to nickname after the method of putting a coin in the strap’s slot became the popular norm. Wearing the penny loafer sockless also became a cool trend at the time, though it is widely debated whether this was due to John F. Kennedy’s influence or the lazy nature of students.
They’ve been cemented as a stylish staple since the 1960’s when a student newspaper at the University of North Carolina published an editorial praising their popularity. Today, they’re still considered a must-have for anyone who wants to stay ahead of the fashion curve.
The Ivy Style wasn’t just exclusive to college students; it was also adapted by working-class GIs and jazz musicians like Miles Davis up to the late 1960s. Davis was regularly seen in the classic Ivy League uniform of the Oxford shirt, khaki chinos, and penny loafers – an ensemble that oozed effortless style. Other iconic figures of the time such as James Dean and Elvis Presley were also often seen sporting penny loafers, cementing their place as a true style staple.
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