First, there was a time when loafers did not exist (there were dinosaurs instead). 

Shortly after, there came a time when loafers did exist, but they were only worn by lawyers and retirees (mostly, it must be noted, retired lawyers).

Somewhere in there the whole Ivy style thing caught on, and suddenly all sorts of people wore loafers! Including, now, aspiring lawyers/retirees. 

But over the last half-decade, loafers have created a new time. A wonderful, perhaps inevitable, time. A time for themselves. A time in which we have become perhaps eternally casual and are getting pretty darn good at it. A time when Blackstock & Weber takes what has long been viewed a stodgy shoe and says “canary yellow pebble grain let’s GO” (and it works). 

This time when just about everything is coming up loafers. 

But…why? And since we’re all now helpless to fall under their shoe-spell, which loafers might be right for you? I spoke with a number of veteran retailers and trustworthy style mavens to get their loafer-based insights, the first and most important of which is: loafers are fantastic, and arguably one of the most essential kinds of footwear anyone can have in their closet.

Alden x David Wood Loden Suede Tassel Loafer

Alden x David Wood Loden Suede Tassel Loafer

First, Though: Defining the Loafer (Plus A Very Brief History)

For our purposes here, a loafer refers to a laceless slip-on shoe that sits below the ankle, and often features some kind of raised seam on the vamp, handsewn or otherwise. Use of the term “loafer” to describe this sort of shoe was supposedly coined by a New Hampshire-based manufacturer called Spaulding Leather Company sometime in the 1930s.

Penny loafers, bit loafers, and tassel loafers are arguably the most prominent subsets of the style. While other slip-ons can certainly be considered part of the loafer canon—Baudoin & Lange’s Belgian loafers, Oak Street’s Slip Moc, and Viberg’s Venetian-style Slipper for example—our attention here is mainly focused on loafers of the penny/bit/tassel variety, The Big Three of the genre.

alden brogue kuro leisure handsewn moccasin

The penny loafer features a strap with a large slit across the top of the vamp.

Carmina Horsebit Loafers In Bourbon Cordovan

The bit loafer features a miniaturized metal horse bit across the vamp.

crockett jones cavendish

The tassel loafer is adorned with a set of tassels, and often features a perimeter lacing around the opening of the shoe.

While there have been many loafer-like slip-on shoes across multiple centuries and continents, the loafer as we know and appreciate today largely surfaced in the early 20th century. The creation of what is perhaps the first modern penny loafer can be credited to a Norwegian shoemaker named Nils Tveranger.

Tveranger spent several years learning shoemaking in America, where he encountered the moccasin shoes made by indigenous people. Later, Tveranger moved to the Norwegian town of Aurland, where local fishermen wore slipper-like teser shoes. Taking inspiration from both Native American and Norwegian footwear, Tveranger designed what came to be known as an Aurland shoe, first introduced around the year 1930. (Aurlands are still produced in Aurland, Norway today.)

aurland shoemaking

Making an Aurland shoe

These Aurland shoes eventually grew quite popular and were exported to many different countries, including the United States. In 1936, G.H. Bass became the first American manufacturer to create a widely popular version of the Norwegian shoe, putting a subtle spin on the design by cutting a broad slit into the strap across the shoe’s saddle—large enough to fit a penny into, which later lent the name “penny loafer” to the style. As a nod to the shoe’s origins, G.H. Bass named their loafers Weejuns (shortened from “Norwegian”).

Other popular loafer styles followed not long after. Supposedly, the tassel loafer was originally designed at the behest of actor Paul Lukas, who came across a pair of oxfords featuring tassels on the laces. Lukas wanted to create his own slip-on spin on the style, and approached a few of American companies to see if they could produce it. Eventually Lukas’s request wound up at Alden Shoe Company. Borrowing the slip-on style and apron of a penny loafer, Alden designed a shoe with a perimeter lacing that terminated at the vamp with a pair of decorative tassels. This style originally debuted sometime around the year 1950.
Alden Tassel Loafer—Shell Cordovan
Meanwhile, the bit loafer was first introduced in 1953 by prominent fashion house Gucci. The Gucci horsebit loafer featured a golden metal miniaturized horse bit (or snaffle—incredible word, why are we not calling these things Snaffle Loafers, people?!?) across the vamp, and it originally came in black to lend it an air of formality (at the time, most loafers were brown and seen as strictly casual wear). While several brands produce their own bit loafers today, “Gucci loafer” is still synonymous with the style for many people.

gucci horsebit loafer

Gucci Bit Loafers

The Enduring Appeal of Loafers

To some, wearing a loafer might feel like a conspicuous signifier of class and age (thanks for reading, retired lawyers!). And to be be fair, it’s difficult to bring up loafers without mentioning how popular they were throughout a great deal of the 20th century with prep school students, Ivy Leaguers, actors, politicians, bankers, and so on. Indeed, magazines like Esquire helped to mythologize the loafer early on as the de rigueur footwear of the elite.

But now, everyone who wants to loafer gets to loafer.

yuketen robs loafer

Yuketen Moccasin Loafers

“I think there’s a generational gap that sometimes looks at loafers as ‘a dad shoe,’ especially tassel loafers,” said Sean Moran, proprietor of menswear shop Dashing Chicago, “until a younger generation inherits a pair, or borrows a pair or simply stumbles upon a model from a modern brand that moves them.”

So why do loafers continue to be a popular choice for so many? The root answers are almost always 1) their versatility, and 2) the increasingly casual nature of dress codes throughout our social spheres.

“As the workplace has become more casual, suits have given way to chinos and black oxfords have given way to loafers. One might say loafers are the dress shoe of the casual age,” remarked George Vlagos, founder of Oak Street Bootmakers.

“They are easy to dress up and down,” said Quentin Brunson, a retail specialist who previously worked for Crockett & Jones in their Jermyn Street location in London. “You can wear the same loafers with khakis or slacks up to a full suit.” Plus they travel quite well. “If you can only pack one pair, they’ll tackle the travels, any meetings or functions you have to attend and even the casual times.”
oak street bootmakers bit loafer black calfskin
Nick Andry, one of the people behind the popular NYC menswear pop-up market Alfargo’s Marketplace, pointed to the loafer’s “unique combination of elegance and an easygoing attitude.”

“While oxfords and boots may come across to some as stodgy or ‘stiff,’” he said, “a well-worn loafer allows the wearer to show off their rebellious attitude (See Tony Sylvester, anyone who wears Belgian loafers outside of Bernie Madoff, etc.) while still looking presentable enough for a boardroom meeting or first date.”

From the perspective of where loafers sit in the pantheon of American fashion, Derek Guy of Die, Workwear! and Put This On posits that “loafers are a quintessential American shoe.”

“The United States has long advocated for a more relaxed, casual approach to men’s style,” he noted. “Even when the lounge suit was popular and became a symbol of upbeat capitalism in the early twentieth century. Americans approached tailoring with more ease than their British counterparts. We advocated for soft-shouldered sack suits, two-piece suits as daywear, rumpled oxford cloth collars, and fabrics like bleeding madras and seersucker.”

alden dashing chicago the fields lhs tassel loafer

Alden x Dashing Chicago—”The Fields” LHS Tassel Loafer

“Later, American style became about five-pocket jeans, t-shirts, double-riders, repurposed military surplus jackets, and youth subcultures like punk and hip hop. So, looking relaxed and casual has always been a part of American style, and the loafer is simply the most casual form of traditional leather shoes. Tassel loafers with business suits were a classic combination for American lawyers; the penny loafer was the sine qua non of the postwar Ivy Look. Camp mocs are also very ‘Maine Guy’ attire. Even Californians have their own version of the slip-on with Vans. Americans just prefer slipping on their shoes.”

Wherein Our Experts Further Extoll the Virtues of Loafers

A question I posed to everyone I spoke with for this story: How would you sell a loafer to someone who has never worn one before?

“Loafers have a louche, carefree character that has always been associated with warm-weather wardrobes,” Derek Guy said. “They’re easy to slip on, easy to slip off. They look great sockless, which is useful on hot days. And they’re just generally more lounge-y than a pair of lace-ups. If your style leans dressy, loafers can also work with everything from smart-casual all the way up to a suit.”

Nick Andry echoed Guy’s sentiment about loafers’ ease of use and adaptability, referring to them as “a cheat code.”

Alden x Brogue California Full Strap Loafer—Navy Nubuck

Alden x Brogue California Full Strap Loafer—Navy Nubuck

“Honestly, I don’t even remember the last non-sneaker lace-ups I bought and wore,” he said. “I always find myself reaching for my slip-ons. I have give or take 12 pairs in various makes and materials in my footwear rotation (I don’t have a problem, I swear!) and I just find them more convenient, comfortable, and frankly, better looking than their laced brethren.”

Keeping with the video game theme, Sean Moran framed loafers as a way to “level up” one’s wardrobe.

“Leave your sneakers at the door, slip on a pair of loafers, and dress up your casual look,” he said. “Just like all shoes don’t fit every occasion, nor does only one pair of loafers. That being said, I think a really stellar modern look is a pair of more refined joggers or drawstring waist trousers, a knit polo, plus a casual sport coat, cardigan, or suede jacket like a Valstarino from Valstar…and a pair of loafers. It’s casual, it’s smart, it shows you made a conscious decision to not skimp on the footwear, and it elevates your look.”

Grant Stone Traveler Penny Loafer in Dune CXL

Grant Stone Traveler Penny Loafer in Dune CXL

George Vlagos had perhaps the most vivid reason why one should consider slipping into a pair of loafers: “Never having worn loafers is somewhat like never having eaten an onion. Sure, a child may be excused from liking onions while their palate develops, but at a certain point you have to be honest and say that without onions, there exists a culinary void which may be illuminated by no other torch. The loafer is a bridge over a chasm of similar depth, between casual and formal, work and leisure, which only a fool would dare cross in sneakers.”

How To Choose The Right Loafer

If you’re ready to jump feet-first into the world of loafers, there are plenty of considerations to make. And there’s lot to choose from out there—not just in terms of general style (penny, tassel, bit, or otherwise), but in terms of specific aesthetics as well. (Put This On’s guide to finding the perfect loafer, written by Derek Guy, illustrates this quite well, and is a fantastic resource.)

Simon Crompton of Permanent Style noted that loafers generally hew towards two different looks: “A loafer can be very elongated, in a very smart leather, and almost pointy, and will be much smarter and flashier. Or, a loafer can have a much rounder toe, a bigger welt, a sort of higher wall on the toe, and look like a sort of traditional American loafer, and much more casual.”

Crompton and others cautioned against buying your first pair of loafers online. “It’s the hardest style of shoe to fit for a lot of people, because you’ve got no means of adjusting the fit,” he explained. “There’s often a bit of a compromise between being held in the back of the shoe around the heel, and having enough space for your toes and comfort in front. For that reason, it’s one which it’s better to buy in-person rather than online, if you can. Try and get some good advice and try different sizes and last shapes, because depending on your foot shape, one will definitely work better than others.”
edward green belgravia dark oak
While there are plenty of different kinds of loafers to choose from that will likely jive with your personal style, there are also ones that can help you mix things up and even move you out of your comfort zone. Sean Moran pointed to tassel loafers in particular as one example.

“Now that’s a challenge for some guys, as they have this ‘old banker’, too stodgy mindset towards the tassel loafer aesthetic,” he said. “I look at it like this: I think about wearing a tassel loafer like I do a bow tie—it’s a small way to present your style and personal identity. It shows you have a personal aesthetic, but can also be a bit playful. I was never of the opinion that a tassel was a pompous or dated aesthetic; I always saw it as a way to show a bit of flair!”
crockett jones harvard 2 khaki suede

Some Favorite Loafers to Consider

When I asked each person what their favorite loafer was, the most popular answer was Alden’s Leisure Handsewn penny loafer, especially model 986 in Color 8 Shell Cordovan.

“It goes with everything, you can dress it up or down,” said Steven Taffel, owner of NYC shoe sanctum Leffot. “I could wear it with a sport coat and a pair of trousers, or jeans or khakis. It’s just super versatile.”

“It’s a bonafide classic for good reason,” agreed Nick Andry. “It’s pretty much the platonic ideal of a classic American loafer. What I most appreciate about them is they aren’t TOO elegant. While I find more refined chisel toe or European loafers beautiful, the slight chunkiness and roundness of the 986 ‘dresses it down’ a bit.”
alden 986 leisure handsewn color 8 shell cordovan
Derek Guy highlighted Edward Green’s Piccadilly in a dark brown leather, especially for pairing with suits and sport coats. “I know the price is staggeringly expensive—you can find them on sale nowadays, or sometimes on eBay—but they really have the ideal shape for tailoring,” he said. Guy also likes the Alden Tassel Loafer in a black leather; he prefers the discontinued Brooks Brothers model, but Alden’s stock version is quite close.

[Oak Street] Bit Mocs are on my feet now,” said George Vlagos, “but I’ve been rotating equally through the Penny Moc and Bit Moc.”
oak street bootmakers bit moc natural chromexcel
Sean Moran said Alden’s 563 Tassel Loafer in Color 8 shell was his “house on fire and had to save one pair” pair. “Dress it up with a suit, slip them on with denim, or cuff your cotton trousers and pair them with some no-shows—it always performs and looks the part!”

“I’ve worn the C&J Harvard in dark brown cordovan for years,” said Quentin Brunson, “and they’ve served me well. I’ve taken them to multiple functions—some formal, some less so.”

Simon Crompton favors the Edward Green Belgravia in a brown suede: “It’s elegant, without being too flash.” Another favorite of his is Alden’s Aberdeen-lasted Full Strap loafer in Color 8 shell, which offers a similar shape but a wholly different look.edward green belgravia dark brown suede

If I Made it This Far, Does That Mean I Have to Buy Loafers?

Totally up to you! But also: yes. You’re in too deep now. Just be sure to take the time to find the right pair for you.

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