Best Way to Wear Slip-on-Shoes or Loafers

Slip-ons are typically tiny, lace-less shoes. The style most commonly used, known as loafer or slippers in American culture, has a moccasin construction. One of the first designs was launched in London by Wildsmith Shoes, the Wildsmith Loafer. They started out as casual shoes but grew in popularity to the point that they were worn in America with business suits.

Another style was introduced as Aurlandskoen (Aurland Shoe) in Norway (early 20th century). In certain cases, they are worn in a number of colors and patterns, frequently featuring tassels on the front or metal decorations (the ‘Gucci’ loafer).

A less informal, earlier style of slip-on is made with a side goring (sometimes called a loafer dress). Made in the same form as Oxford’s lace-ups, but without laces, these shoes have elasticated side inserts that allow the shoe to be removed easily but remain snug when worn. This cut has the greatest success in Britain.

History of Loafers

A pair of slip-on shoes from Matalan

A pair of slip-on shoes from Matalan

The London-based bespoke shoe company, founded in 1847[disputed – discuss], created the first loafer as a country house shoe for the landed gentry and the royal family. The “Wildsmith Loafer” by Raymond Lewis Wildsmith of Wildsmith Shoes was designed for King George VI as a casual house shoe. Subsequently, the shoe was advertised and distributed by other London shoe companies and called “The Harrow.”

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The word pennies loafer has unclear beginnings. One theory is that in the 1950s, American prep school women, wanting to make a fashion statement, took a penny to put into the diamond-shaped slit on their Weejuns. Another hypothesis is that two pennies might be inserted into the slit, enough money to make an emergency call in the 1930s. This, however, is an urban legend, as pay phone calls in the US have never been less than five cents, nor have payphones ever accepted pennies.

Manufacturing of Aurlandsko in Aurland around 1950.

Manufacturing of Aurlandsko in Aurland around 1950.

Either way, the term Penny Loafer has been applied to this slip-on style and has been stuck since then. The practice continues, particularly among those who remain committed to a classical and polished but still scholarly appearance, such as lawyers.

In the mid-1950s, more continental influences introduced a more sophisticated picture to light, lower-cut slip-ons, which shifted from strictly casual use to suit pairing in the 1960s (but still only in America). In 1966, Italian designer Gucci took the next step of adding a metal strap across the front in the form of a horse snaffle bit. These Gucci loafers (now a generic term referring to shoes of this type by any manufacturer) also spread across the Atlantic and were worn by businessmen in the 1970s, becoming almost a Wall Street standard, with widespread use in the 1980s.

At the beginning of the twenty-first century, the revival of the Penny Loafers, whose popularity peaked between the mid-1960s and again between the early 1980s and the early 1990s,[citation needed] took place, with the shoe emerging in a more durable form, similar to the original model, either moccasins or espadrilles, all of these types being very low or flat without heels. The revival was most evident at college campuses across America.

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The tassel loafer, which originated in the 1950s, is another variant of the basic style. Again, though informal, their gradual recognition among the American East Coast prep school community as equal to the brogues (wingtips), led them to wear suits there, where they became synonymous with business and legal classes.

Types of Loafers

StyleYearHistoryDefining Features
Wildsmith1926Raymond Lewis Wildsmith was asked to make a country house shoe. Originally named the 582, now commonly known as the Loafer Wildsmith.Serred seam and strengthened toe case. Vertical stitching on your toe.
Aurland1930Shoemaker Nils Gregoriussen Tveranger mixed the Native American moccasin with the shoes worn by local fishermen in Aurland, Norway. The Moccasin of Aurland was born.Raised seam on the end, similar to moccasin. Narrow cut out of the saddle.
Penny1936Oh, G.H. Bass of Wilton, Maine, introduced a loafer named 'Weejun' ('Norwegian'). It became very popular in the U.S., particularly among prep school students, whose legendary states held pennies in the saddle slot for pay phone calls. This is the term 'penny loafers.'Leather saddle strap across the end, cut out long enough to carry a penny.
Kilted1950sFor over 100 years, Kilties has been fashioned on brogues and Oxfords by Scottish ghillies, kings and golfers. The loafer was kilted in the 1950s, when Kiltie's golf shoes and penny loafers were in their zenith trend. It's also popular with Mods and skinheads.Kilt-style over-the-vamp flap, covered with a leather cord or a tassel.
Gucci1953Italian designer Aldo Gucci simplified the shapes, added a bit of gold horse and made it black. This raised the loafer to the status of formal wear.Metal-style horse bit connexion.
Belgian1954Henri Bendel sold his family shoe shop and purchased two 300yr old shoe factories in Belgium. His loafers were immediately struck, and the bow was easily identifiable. His job has won him two knighthoods.Small bow on top and sewn inside out to make a fine seam.
Tasseled1957Brooks Brothers and Alden Shoe Co have partnered in the development of the famous tasselled loafer. Originally the commission of the actor Paul Lukas, who liked the tasselled shoelaces on a couple of Oxfords.Tassels held in place by a strand of leather.

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Use of Loafers

In the United States and some European countries, such as Italy, loafers are commonly used as casual and casual shoes worn for work and leisure, while lace-ups are still preferred for more formal situations. The general popularity of brown over black is applied to loafers, often using exotic leathers such as suede and cordovan. Socks have been optional when wearing loafers since the early 1980s.

While originally men’s shoes, some types of loafers, such as casual tassels and pennies loafers, are worn by women as well. Women’s loafers appear to have shorter toes and wear a variety of outfits, from shorts, jeans, slacks, and capris to dresses and skirts.

Final Thoughts

Loafers come in a range of types and fabrics, from casual moccasin to formal, patent leather tuxedo loafers. Consider your outfit’s color, pattern, and silhouette when choosing which loafers to wear. Enjoy the addition of loafers to your wardrobe with some color hints, shoe design, and dress code. Search for your brand and choose which suits you the best.

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