The Ultimate Loafer Shoes Guide For Men

In this series on men’s footwear, we have previously presented a guide to Moccasins and the Driving Moc, which is related to the loafer, but not the same. What exactly is a loafer, then? In this guide, you will learn all about loafers, their different styles, and the history of this wonderful shoe. Loafer Guide for Men […]

In this series on men’s footwear, we have previously presented a guide to Moccasins and the Driving Moc, which is related to the loafer, but not the same. What exactly is a loafer, then? In this guide, you will learn all about loafers, their different styles, and the history of this wonderful shoe.

Loafer Guide for Men (Video)

Before we dive into the history of the loafer, let’s set a few ground rules for what distinguishes this type of footwear from other slip-on styles.

Penny Loafers by Rancourt
Penny Loafers by Rancourt

Characteristics of a Loafer

  1. A loafer has no laces; in other words, it’s a slip-on shoe.
  2. A loafer is a “low shoe,” meaning that the ankle is exposed, and the shoe does not wrap snugly around it.
  3. The sole of a loafer is separate from its upper.
  4. Loafers often feature heels with a relatively low profile.
  5. The upper vamp has a moccasin-like construction.
  6. Loafers will sometimes (though not always) feature a piece of leather across the vamp, which is known as a saddle.

From the above description, one can see the similarities between a moccasin and a loafer. However, there are a few key differences:

  1. All loafers have a separate sole; this is not the case for the majority of moccasins.
  2. Similarly, loafers have a defined heel, while moccasins do not.
  3. Unlike moccasins, loafers lack embroidery, beading or other ornamentation on the uppers.

The last difference is the primary reason these shoes, though similar in many ways, evolved into two different and distinct types of footwear. Important to note is that loafers and moccasins developed on separate continents. For more, here’s an historical overview.

Weejuns in the 1960's - a symbol of elegant leisure
Weejuns in the 1960’s – a symbol of elegant leisure

History of the Loafer

Unlike most other shoes, the loafer has multiple origin stories. One such story is that the loafer came directly from the moccasin, thus adding to the confusion. However, menswear and clothing historians are largely in consensus that loafers:

  1. Came from an English royal commission for a new form of house shoe, and/or
  2. Had their beginnings when a Norwegian man, Nils Gregoriusson Tveranger, hybridized traditional Native American and Norwegian footwear.

While it is comparatively difficult to pinpoint the definitive origin of the loafer compared to other types of shoes and boots, its evolution is still quite interesting. For purposes of clarity, this article subdivides the history of the loafer based on types while maintaining a rough timeline.

Wildsmith loafer in brown with Moccasin construction and typical saddle
Wildsmith loafer in brown with Moccasin construction and typical saddle

The Wildsmith Loafer

in 1847, Matthew and Rebecca Wildsmith established a footwear manufacturing business in London by the name of Wildsmith Shoes. The mainstay of their business was making and subsequently repairing boots for the Household Cavalry, whose mounted unit, the Household Cavalry Mounted Regiment, was part of the Monarch’s official bodyguards.

Covent derby brown leather with U Broguing by Wildsmith
A “Covent” brogue derby shoe in brown leather by Wildsmith Shoes

In 1926, Matthew and Rebecca’s grandson, Raymond Lewis Wildsmith, was commissioned by King George VI, to make a country house shoe that he could wear mostly indoors with his shooting hose. Raymond came up with a low-heeled design that did not include laces and which could be comfortably slipped on and off. The construction of this shoe had a lot in common with the moccasin, though it’s unknown whether Raymond was familiar with that related style, or if he came up with the design based on the very specific instructions he received. This design soon appeared in his ready-to-wear collection as the 582 (later the Model 98). Today, the style is known simply as the Wildsmith Loafer. While they were designed for indoor wear in a casual fashion, they very soon gained in popularity and began to be worn as a casual choice for outdoor wear.

The Aurland Loafer from Norway & Hand Drawn Moccasin Model for Reorder by Gardner
The Aurland Loafer from Norway & Hand Drawn Moccasin Model for Reorder by Gardner

The Aurland Loafer

At the beginning of the 20th century, Shoemaker Nils Gregoriusson Tveranger (1874-1953) introduced a loafer in the town of Aurland, Norway. Nils had traveled to North America at the age of thirteen to learn the art of shoemaking, and spent approximately seven years there. In 1930, he introduced a new design with heels which came to be known as the “Aurland moccasin.” This design was influenced by two sources: the moccasins worn by the Iroquois tribe of North America, and the traditional, moccasin-like shoes worn by the fishermen in his hometown of Aurland.

Penny Loafers from Aurlands in black leather. [Image Courtesy: Aurlands]
Penny Loafers from Aurlands in black leather. [Image Courtesy: Aurlands]

He slowly started marketing his design in the rest of Europe, where it became extremely popular. At that time, many Americans began traveling to Europe, where they stumbled upon these shoes, took a fancy to them, and brought a pair home. They came to the notice of the editor of Esquire magazine, and the publication began promoting them. Around 1933, the Spaulding family of New Hampshire sensed a business opportunity and started making shoes based on the Aurland Moccasin. They named their product the “Loafer,” which was by that point a generic name for slip-on shoes in America.

Around 1940, industrialist and U.S. Secretary of the Treasury Arthur Gardner bought a pair of Aurland shoes. Later, when he was unable to obtain them in the U.S., he made an unusual request to the Norwegian ambassador, providing him with a sketch of the “slippers”. Apparently, Gardner did not know where the shoes were made, but the ambassador recognized that he must have been referring to Aurland shoes. The local mayor organized production and three months afterward, four pairs of ”moccasins” were mailed to Washington, D.C.

Crockett & Jones Penny Loaffer Model Boston in Scotch grain calf on a classic Last & Variation Mertin on a more modern last
Crockett & Jones Penny Loafer Model Boston in Scotch grain calf on a classic Last & Variation Mertin on a more modern last

The Penny Loafer

In 1936 (some sources put the date as 1934), the G.H. Bass shoe company introduced its version of the loafer, and the company is known for it to this day. Their design included a distinctive strip of leather (the saddle) of the shoe with a diamond-shaped cutout. Bass gave their loafers the name “Weejuns,” to sound like Norwegians – a nod to the Norwegian roots of the shoe, and to differentiate them from the Spaulding loafer. Weejuns became immensely popular in America, especially among the Prep School students in the 1950s, who coined the term “penny loafer.” Legend has it that, wishing to make a fashion statement, they took to inserting a penny into the diamond shaped cutout of their Weejuns. An alternate theory is that, in the 1930s, two pennies were sufficient to make an emergency telephone call.

Bass Weejuns - Made in Maine Reddish Brown & Olive Green
Bass Weejuns – Made in Maine Reddish Brown & Olive Green

Whatever its origins, the name “penny loafer” stuck, and the G.H. Bass penny loafer has achieved the status of a classic, and is a staple of Prep and Ivy Style. In 1937, the American brand Nettleton trademarked the term “loafer” for “Ladies’, Men’s, and boys’ shoes made of leather, rubber, fabric, and various combinations of such materials.”

Penny Loafers - Rogers Peet Company & Bass Weejuns 1965Penny Loafer by Dexter

In the 1930s the Duke of Windsor was a big proponent of penny loafers, and he often wore a brown and white two-tone Penny Loafer with his suits.

The Tassel Loafer

It remains unclear what the roots of the tassel loafers are. Alan Flusser has claimed tassel loafers were popular with the Ivy League set in the 1920s, though our research has been unable to corroborate this. U.S. President Harry Truman wore derby shoes with tassels, but he did not have tassel loafers. Rather, evidence suggests that after the end of the Second World War, the little-remembered but rather debonair American movie actor Paul Lukas bought a pair of oxfords with little tassels at the end of the laces while on a trip abroad. Upon his return to America, he took the shoes to the New York shoemakers, Farkas & Kovacs, and asked them to make something similar. Not fully satisfied, Lukas then took them to Lefcourt of New York and Morris Bookmakers of Beverly Hills. Ironically, both of these firms would pass on the request to the Alden Shoe Company.

Alden Tassel Loafer
Alden Tassel Loafer

The then-president of Alden, Arthur Tarlow Sr., Came up with a slip-on pattern keeping the leather lace and tassel as a decoration. Alden, realizing the potential of the shoe, continued to experiment with the design for another year, finally launching it in 1950 through Lefcourt and Morris stores. The “tassel loafer,” as it became to be called, was a success, finding favor with the sophisticated set of New York and Los Angles. In 1957, Brooks Brothers approached Alden to make a line of tassel loafers especially for them. The resultant design was a tassel loafer with a decorative seam at the back part of the shoe which, to this day, remains exclusive to Brooks Brothers.

The Gucci Loafer

While the loafer grew in stature in America, with the tassel loafer being worn with suits by the 1960s, it was not quite the same story in Europe. In Italy this style of shoe was more widespread, but all other Europeans considered the loafer to be a casual shoe that had no place in the city. However, things changed in 1968 when the Italian designer Gucci introduced a loafer with a golden brass strap in the shape of a horse’s snaffle bit across the front–in keeping with the company’s saddle-making heritage. Gucci opened his New York office in 1953 and noticed the popularity of the loafer. He refined the lines, added the bit, and made them in black (loafers were usually in brown in keeping with their status of being a casual shoe).

The Gucci Horsebit Loafer
The Gucci Horsebit Loafer

The result was a shoe with just enough formality to make it acceptable to be worn with suits. These went on to be named the “Gucci loafer” and helped establish the loafer in Europe and across the globe. Gianni Agnelli and John F. Kennedy were just a few of the big supporters that helped to popularize the style. In 1969, Gucci sold 84,000 pairs of loafers just in their U.S. stores. In keeping with the continued journey of the loafer, it crossed the pond to America, where it was adopted by 1970s businessmen and almost became a uniform on Wall Street.

In case you shop at amazon and we refer you, prices are the same as normal, we just get a small commission.
Douglas Fairbanks, Jr., wearing Gucci loafersClassic Gucci Loafers in Black Leather

Until Gucci designed this loafer, it was a brand known merely to insiders who appreciated saddles and quality luggage. The men’s loafer known as the Model 175 was designed in the mid-1950s. Initially, it sold for approximately $14. Subsequently, Gucci developed the Loafer Model 360 for women, and the very similar model 350, which was offered in seven unusual colors. Consequently, the fashion journalist and critic Hebe Dorsey dedicated an entire article to the shoe which was published in the International Herald Tribune and made the shoe an overnight success. Since 1985, the Gucci Loafer has been part of the permanent exhibition of the Metropolitan Museum of Art in New York.

The Belgian Loafer

Another popular style is the so-called “Belgian loafer,” invented in the 1950s by Henri Bendel, whose family store also brought Chanel, Dior and Balenciaga shoes to the U.S. Its characteristic features were:

  • A small bow that was easily recognized
  • Soft-sole construction; the shoe was sewn inside-out
  • Unusual colors and materials

After the Bendel family sold their store in 1954, Bendel purchased two 300-year-old shoe factories in Belgium in 1956 and started producing men’s and women’s loafers. The shoe became an instant hit, and the bow was easily recognizable. As such, he single-handedly rescued the Belgium shoe industry, which earned him a Knightship of the Order of Leopold I in 1964. Just six years later he was made Knight Commander of the Order of Leopold II.

Belgian Loafer
Belgian Loafer

Bendel died in 1997, and although the shoes are sold around the world, the only retail store that carries Belgian Loafers is located at 110 East 55th Street in NYC. Of course, you can also find them online. If you enjoy extravagant shoes, Belgian Shoes may be the right fit for you.

Loafer Construction

Since loafers are casual shoes, most of them are Blake- or Blake-rapid-stitched, though you may occasionally find Goodyear-welted loafers. While these are a little heavier, they offer an additional layer of cork, which makes walking in them a bit more comfortable. For casual summer use, an unlined, Blake-stitched loafer might be the better choice if you don’t intend to walk much in them. On the other hand, if you are looking for a more robust, multi-season loafer, a Goodyear-welted version with leather lining is probably the better choice. Twice a year Gucci releases a new version of their loafers, and while the summer ones are unlined and made of very thin leather, the fall-winter collection is leather lined and made of thicker leathers.

Slip-Ons – Not Loafers

Many men and women confuse slip-on shoes with loafers. As the name suggests, you can slip on the shoe just like a loafer, but it lacks the moccasin seam on the uppers and looks more like a regular oxford or brogue. The slip-on is favored by men who wear business suits when they fly because you can easily pass security and unlike a loafer, it is appropriate with a pinstripe business suit.

Slip on Shoe - Not a Loafer because it lacks the Moccasin construction
Slip on Shoe – Not a Loafer because it lacks the Moccasin construction

Loafer Style Advice

The Loafer is a piece of footwear that straddles the two worlds of casual and a more formal style, making it quite a unique piece in that respect. No matter what you read, a loafer is never a truly formal shoe because of its casual heritage.

Scarosso Model Mezzano Tassel Loafer in black suede with red tassels
Scarosso Model Mezzano Tassel Loafer in black suede with red tassels

Gucci Loafers

Gucci loafers are often combined with all sorts of outfits. Of course, using a black, polished box calf leather with leather lining and refining the shape will make the loafer more formal than an off-white, unlined Gucci summer loafer in suede, but at the end of the day, it is still a loafer and not suited for tuxedos or white tie ensembles. Likewise, it is historically not appropriate to wear one with a classic three-piece business suit simply because it is too casual. On the other hand, a casual suit will look just fine with tassels.

Selection of worn out Gucci Loafers
Selection of worn out Gucci Loafers

Tassel Loafers

Many American businessmen over 50 will wear business suits or sport coats with slacks and black or brown tassel loafers. As a rule of thumb, black or oxblood tassel loafers are about as formal as a navy blazer with grey flannel slacks. Wearing tassel loafers with business suits would probably not be considered to be a faux pas, but we would still encourage you to wear them with casual suits or blazer/sport coat combinations and choose an Oxford with more formal garments.

Duke of Windsor in suit with bow tie, hat and two tone Penny LoafersThree Two Tone Penny Loafers and one pair of brown Tassel Loafers in the Duke of Windsor's Shoe ClosetDuke of Windsor with two tone Penny Loafers

Penny Loafers

Penny loafers are a perfect companion for corduroy pants, chinos, flannel slacks and in the summer even linen or seersucker. In terms of formality, they rank just slightly below a tassel loafer and are a great companion for a blazer outfit with Oxford shirts and a tie or bow tie.

Penny Loafers are versatile
Penny Loafers are versatile

In a casual setting, the loafer can replace any of your other casual shoes to add a bit of dash to your look. However, unlike Boat Shoes, it is recommended that you keep your socks on when you wear loafers. Casual loafers can be worn with denim and khakis, and some men even wear them sockless with shorts. The beauty of rules is that you can break them elegantly once you have mastered them.

What Loafers Should You Buy?

Every man should have at least one pair of loafers. With that said, there is not one style that is objectively more necessary than another. While some would consider the penny loafer or Gucci loafer the number one choice, we would argue that tassel loafers make a good first pair; they can be worn in any situation where the other styles could, but the tassels will add a unique touch to your wardrobe. Here are a few options for purchasing loafers:

Penny Loafers

If you want to invest in a penny loafer, you have many options. Bass Weejuns offers foreign-made models for $118, Made in Maine versions for $295, and about twice as much for shell cordovan. Apart from that, you can also find them from Allen Edmonds ($225 – $365), Alden ($498), Rancourt ($225), and Brooks Brothers ($198). For a more high-end interpretation of this style, take a look at Gaziano Girling. In Europe, Jay Butler offers an affordable RTW option for under $150, and Crockett & Jones offers a large selection of different styles and lasts.

Monaco Penny Loafer & Variation by Gaziano Girling
Monaco Penny Loafer & Variation by Gaziano Girling

Tassel Loafers

All the brands mentioned above produce tassel loafers as well. Also, Meermin offers interesting budget tassels; Scarosso has an affordable MTO Program, though their offerings would not technically be considered loafers. For an excellent selection of various penny and tassel loafers, take a look at Pediwear.

Gucci Loafers in the 1970sEarly Gucci Loafers

Gucci Loafers

Although copied many times, Gucci is still the originator of the shoe. Bear in mind that they issue many different versions in gold and silver horsebit hardware. Priced between around $450 – $630, you certainly pay much more for the brand name than for the quality of leather and workmanship. We’d suggest that you invest that kind of money into higher quality and buy from places like those mentioned above, but to each their own. If you want a Gucci loafer, the most classic bit loafer is black leather with gold hardware, which sells for $590. For a more affordable version, check out Jay Butler, which sells them for just $175, which is great value for the money.

our Conclusions on Loafers

With this knowledge of the loafer’s rich history and many variations, what are your thoughts about this versatile shoe? Do you have a favorite variety, and how do you wear them? Let us know in the comments below.

The Ultimate Loafer Guide - Penny Loafers, Tassels & Gucci
Article Name
The Ultimate Loafer Guide – Penny Loafers, Tassels & Gucci
Learn all about Loafers including the Penny Loafer, Tassels & Gucci Loafers, including history, designs, construction & what to buy.
Gentleman’s Gazette LLC
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Gentleman's Gazette LLC

Sammy Singh

Graduate of UCLA and Wharton School of Business and Media Personality. World renowned global entrepreneur, venture capitalist, financial technology professional, tax specialist, marketing mogul, and more! Connect with me at:

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