How to choose the perfect loafer A guide to the main models and constructions of the most popular shoe of recent years

In recent years, the loafer has become the new gold standard of men's footwear. For decades, the loafer was considered an "old man's" shoe, but around ten years ago, with the boom of Gucci under Alessandro Michele, the idea that a loafer could be worn with jeans entered the collective consciousness. Within a few years, the more grown-up loafer eclipsed the youthful sneaker without making the outfits it featured in any more casual. On the contrary, it was the loafer itself that "casualized" and replaced the sneaker — so much so that its inclusion in a wardrobe has become a kind of implicit rite of passage from a more adolescent style to a more mature one.

Now, before discussing the various loafer styles that exist, a few distinctions are in order. First, one must distinguish between "moccasin" and "loafer," even though in Italian the former term is always used. Strictly speaking, a moccasin is a leather shoe in which the hide runs up the sides of the foot and closes with a piece applied to the toe called an apron. The U-shaped closure where the toe leather is straight is called a moc-toe (short for mocassin toe). The difference from the loafer is that the original moccasin has no separate sole or heel, and is therefore represented today by driving shoes and slippers. The more common loafer has a separate sole and heel.

An important distinction concerns the toe of the loafer. The rounder and shorter the toe (think classic Sebago or G.H. Bass), the more casual the loafer is considered. When the toe is elongated or almond-shaped, with a smaller apron pulled back from the actual tip of the shoe, the loafer becomes more formal. Furthermore, the casual style often features the classic penny loafer strap (as we will see shortly), while the absence of a strap is characteristic of more formal models. More generally, if the front seam remains visible, the shoe is casual or daytime wear; when the front seam is concealed using the so-called Adler stitch, we are looking at a formal or evening loafer. But what are the different types of loafer?

The Penny Loafer

The most popular model of all is the penny loafer, recognizable by its strap or "saddle" — a band of leather crossing the vamp with a diamond- or crescent-shaped slot in the center. It features a visible moc toe at the front, a low heel, and a separate leather sole. The silhouette is clean and the upper is often unlined. Along the sides of many American models runs the so-called beefroll, the rolled stitching of the seam joining the pieces, which was introduced by Sebago.

Several versions of its history circulate. In 1936, G.H. Bass launched its version, called "Weejuns" as a nod to the word "Norwegians" — a tribute to the Norwegian roots of the style and a way to distinguish it from the loafer made by competitor Spalding. In 1937, the brand Nettleton registered the term "loafer" in the United States. The Duke of Windsor wore them with suits, in a two-tone brown and white version. The name "penny" emerged in the 1950s among American college students, who would slip a coin into the slot. According to urban legend, this was to make emergency phone calls, but it is just that — a legend — since Bell System payphones of the era required dimes, not pennies. The habit was purely stylistic, as the strap itself was added for purely decorative purposes.

In recent years, partly thanks to The Row and Saint Laurent, the "ruched loafer" has grown in popularity. Its defining feature is a very soft leather upper (suede, nappa, unlined calf, and even eel skin), with the front piece stitched so that the leather gathers into small folds along the apron line. The sides of the shoe are low and unstructured, the sole is thin, the heel almost nonexistent, and the toe line is long and clean. It usually features the strap, but no tassels or metal hardware.

The Horsebit Loafer

Imitated to death yet unable to dent the myth of the original Gucci Horsebit, this model is identical to the penny loafer but, in place of the strap, features a metal bit or "horsebit," usually in brass, whose shape echoes a horse's snaffle bit. Beneath the bit, the shoe is a clean loafer with a thin sole — almost always leather — and an upper in smooth leather or suede. The formal version comes in shiny black leather with a lining.

The Horsebit was born when Gucci opened in New York in 1953. Aldo Gucci noticed the success of loafers, refined the silhouette, added a gold-tone bit recalling the brand's saddlery heritage, and produced them in black rather than the usual brown. By 1969, Gucci was selling 84,000 pairs a year in American stores alone. Since 1985, the loafer has been part of the permanent collection of the MoMA. The generic term "horsebit loafer" came about when other brands began producing models with the same detail.

The Tassel Loafer and the Kilted Loafer

The tassel loafer features two small leather tassels on the vamp, usually at the ends of a lace threaded through the upper. It is considered more elegant, typically comes in models with a more almond-shaped toe (though not always), and can sometimes be found in velvet or exotic leathers. Stylistically, these loafers sit slightly higher on the formality scale, so one should avoid both models that are too casual and simply decorated with tassels, and those in which the leather is not of good quality. In short, if you buy them, it is best they are not cheap. With the appropriate (and deliberate) exceptions, they should be considered unsuitable for a casual outfit.

As for their origin, the story goes that after the Second World War, actor Paul Lukas bought a pair of oxfords abroad with tassels on the laces. Back in the United States, he asked several cobblers to reproduce them, and the request eventually reached the firm Alden. President Arthur Tarlow Sr. devised a slip-on model that retained the lace and tassel as decoration and launched it in 1950. In 1957, Brooks Brothers asked Alden for an exclusive line, featuring a decorative stitch on the back of the shoe that remains a brand exclusive to this day.

Belonging to the same family, the kilted loafer features, in place of tassels, a kiltie — a leather flap with fringe that covers the strap and, in some versions, can also cover any laces or tassels. They are a style much loved by Miuccia Prada, who has revisited them frequently. Some models also add brogue-style perforations to the leather. Their name evokes the Scottish kilt, but the fringed detail was used in the 1950s on Oxford shoes as a flap that shielded the lacing from mud or water when playing golf.

The Belgian Loafer

The Belgian loafer is an extremely low-profile shoe and almost always unlined. It is characterized by a very soft upper with a one-piece almond-shaped apron. The construction of the shoe is nearly deconstructed, with very low side walls, and the overall build is particularly soft and flexible. It may or may not be decorated with a very small, slim decorative bow, often in leather. It is typically made using a distinctive technique: the cobbler stitches a second piece of leather beneath the upper and then turns the whole thing inside out, so that the almond-shaped seam emerges already finished.

An interesting historical footnote is that this model is called "Belgian" but its story is more American. It was created by Henri Bendel in 1955, who popularized it through the Belgian Shoes boutique in Manhattan. Bendel purchased two factories in Izegem with 300 years of history and began producing hand-stitched men's and women's loafers. For having saved the Belgian footwear industry, he was even appointed a Knight of the Order of Leopold I in 1964. The originals are slim and nearly unlined, while many imitators use Blake construction or glued soles.

The Wildsmith Loafer

The Wildsmith is a thoroughbred English loafer and, beyond all variations and decorations, the most formal loafer style of all. It is known for its serrated edge stitching, which keeps the seam on the upper flat, the reinforced toe, and above all the vertical seam, which is its true hallmark. It features the typical strap and a construction close to that of a moccasin. Today Wildsmith produces it using Blake construction, which makes the shoe lighter with a cleaner profile. The brand's signature is a diamond-shaped punch mark present on every pair.

This model predates even the G.H. Bass. It was created in 1926 by Raymond Lewis Wildsmith, who made a bespoke country house shoe for a member of the British royal family, intended to be worn indoors with hunting stockings. Sources are not entirely in agreement on the recipient: some point to George V, others — including the official Wildsmith website — to George VI, at the time still the Duke of York. The model was initially called the 582, then the Model 98, and eventually became known as the "Wildsmith Loafer." It represented the first true introduction of the English-style loafer to London. The Wildsmith shoemaking firm had been founded in 1847 and initially focused on making and repairing boots for the Household Cavalry. Other London shoemakers later adopted the same model and sold it under the name "Harrow."

The Boat Shoe

Perhaps among the most iconic models — and strictly a summer shoe — the boat shoe typically features a white rubber sole with herringbone-pattern siping. The original model is called the Top-Sider and was born in 1935 with a canvas upper, white sole, and herringbone pattern, designed to avoid leaving dark marks on a boat's deck. The siping draws on the siping process (cutting grooves into soles) invented and patented in the 1920s by John Sipe, which Paul Sperry refined into a herringbone pattern.

The idea came to Sperry in the winter of 1935, when he watched his cocker spaniel Prince run across ice without slipping — a year after he himself had fallen off the deck of his boat in Long Island Sound. In 1937 he filed a patent application for the non-slip sole and also introduced the leather version with its distinctive "saddle" and rawhide laces that wrap around the entire shoe, cinching around the foot and heel (they are typically adjusted just once). The name Top-Sider indicates that the shoe allows you to stay "topside," meaning on deck. The sole design was later adopted by the U.S. Navy, and the boat shoe became a classic of American preppy style.