Any discussion of the loafer must begin in Norway. While the majority of Europe’s men donned laced boots and oxfords in the mid-19th Century, Norwegians in some fishing villages sported leather slip-ons, called tesers, as part of their traditional dress. A somewhat archaic penny loafer, these shoes looked like a buckle-less version of a “pilgrim’s” shoe as we think of it today. One such Norweigan, Nils Gregoriusson Tveranger sought to improve this traditional design. In 1908, at age 13, he left his hometown of Aurland to study cobbling in the United States. Just two years later, Tveranger created a patent and design for the “Aurland moccasin,” and premiered the design at Norway’s Bergen Exhibition of 1910. The design combined Norwegian tesers with the style elements from moccasins worn by Iroquois Native Americans, an influence from Tveranger’s time studying American art and history in the US.

The turn of the century also saw the import of European souvenirs, first by wealthy Lost Generation Americans on holiday, then by vendors hoping to mass-market traditional costumes to the US. Aran knits from Ireland, Breton knits from France, espadrilles from Spain and plaid from Scotland, were often woven into a modern cosmopolitan man’s wardrobe. So when English and American sportsmen arrived in Norway to embark on salmon fishing trips, Aurland shoes were the perfect—well...appropriative—fashion souvenir to take back home. Once seeing these styles hit Western shores, fashion entrepreneurs and opportunistic businessmen recognized that the loafer would perfectly satisfy the growing desire for comfort in clothing, shoemakers copied the style and marketed it as a Norwegian look.

Foremost among the mainstream pioneers was the Bass Weejun shoe, from Maine-based G.H. Bass, which featured a strip of leather stitched across the saddle of the shoe and a crescent moon design. Bass debuted the shoe in 1936, shortening Norwegian to “Weejun,” a strange, but memorable corruption of Tveranger’s nationality. Across the pond, British cobbler, Raymond Lewis Wildsmith, created a bespoke country house shoe for King George VI, which found footing in a ready-to-wear collection for non-royals by the mid-1930s.

According to Esquire, the late 1930s gave way to a new loafer look. It was common to see members of the well-travelled leisure class pair loafers with panama hats and dramatically-cut light suits in locales like Palm Beach. But, it wasn’t until the 1940s that the loafer began its place as the dominant stalwart of the collegiate footwear scene.

Loafers earned their place in Ivy Leaguers’ hearts due to their nonchalant vibe, slip-on convenience, relatively low price, and year-round functionality. T Magazine notes that duct tape was often used to hold together a beloved and overworn pair. Socks were foregone in exchange for getting to class on time and pennies were often inserted in the cutout on top. Yet, the origins of the now-named penny loafers’ penny slipping tradition remain completely lost to time. Some believe that one or two pennies were the price of a piece of candy during the style’s heyday while others have cited a penny as enough for an emergency phone call. The rumor that a penny inserted in a loafer with one’s birth year would bring the wearer good luck is persistent, but unsourced and probably untrue.

The 1950s saw celebrities like J.F.K., Miles Davis and James Dean don Weejuns and other classic knockoffs, now available in a variety of colors and materials, like suede and patent leather. Kilties, the more elegant and ostentatious cousin of the penny loafer saw popularity on the fairway and with Mods in England with their tasseled ornamentation. In 1957, Brooks Brothers and Alden shoes collaborated to create their own version of the tasseled loafer, inspired by a commission from actor, Paul Lukas (often remembered for his role in 20,000 Leagues Under the Sea). It is also important to note that around this time, the pejorative term, “tasseled loafer,” became slang to mean “a lawyer,” but the origins are unknown.

Yes, the loafer embodied a no-fucks, “one-percenter on a day-off” attitude. But how would it come to dominate red carpets and formal affairs? And how would it come to be adopted by Wall Street and on-duty politicians? For that, we look to Gucci. While hippies abandoned their collegiate looks for counterculture styles, other college graduates, entering the professional world, hoped to hold onto comforts of their college years. Italian designer Guccio Gucci recognized this, and used black leather and refined lines to execute his idea. Recalling his time working at the Savoy Hotel as a young man, where he would overhear wealthy visitors speaking about polo and horse racing, Gucci added equestrian details to his loafers. The now iconic horsebit buckle elevated the loafer to a luxury item and when it debuted in 1953, owning a pair became a status symbol.

With these pillars of loafer design cemented in the first half of the 20th century, twists on the basic look and re-branding of existing styles began in the second half. The 1970s saw men pairing platform and heeled loafers with bell bottoms, and the 1980s (and the emergence of “preppy” culture) saw young people adopting classic loafer looks. Loafers worn by power brokers and wolves of Wall Street often referred to their loafers as “deal sledders

The late ‘90s and mid-2000s welcomed new, rougher attempts at rebranding the loafer. The Sperry Top-Sider, although more of a boating shoe with laces, is the logical extension of this trend. Loafer-meets-sneaker combo designs, from more pedestrian stores like Kenneth Cole, featured prominent rubber patches and upturned toes. Though looking at them now may cause a cringing shudder, it’s only a matter of time before these styles come back into fashion.

Following Alessandro Michele’s appointment as Gucci’s creative director in 2015 (along with a shadow team of millennial designers), Gucci updated the classic loafer with a sleeker shape and added rabbit or kangaroo fur to some styles. Soon, it felt like every menswear aficionado had a pair peeking out from their cuffed trousers. In the last two years, Wiz Khalifa, A$AP Rocky and Bruno Mars have all rocked variations on Michele’s rebrand.

Prior to the reveal of his long-standing issues with inappropriate sexual conduct at NBC revealed at the end of last month, Matt Lauer sparked outrage in 2016 while interviewing Ryan Lochte about the Rio Olympics wearing loafers without socks. Twitter found his exposed ankles grotesque and unprofessional. Maybe viewers found Lauer’s footwear choice a bit too freeing. But with loafers, an unabashed and slightly offensive freedom is exactly the point. Perhaps that’s why the style is perfectly American. It’s outlasted over one hundred years of fashion changes and trend waves while remaining ubiquitously true to itself.