How to Wear Loafers For Men

Perhaps no other men’s dress shoe has as many stylistic variations as does the loafer, a special member of the “slip-on” class of shoes.

The general school of thought is that loafers should be relegated to casual looks, but that’s not necessarily true.

Depending on the shape of the vamp, type of ornamentation, silhouette, stitching and material, the loafer can be worn with a wide variety of outfits.

(A rule of thumb with any type of men’s footwear is that leather is more dressy or formal than suede.)

History of the Loafer

Before we delve into what types of loafers go with what types of looks, let’s take a trip back in time to get a glimpse of how the loafer actually came to be. 

We’ll actually be taking a forked road, so to speak, as there are two stories on how this now popular style was born.

The first tale recounts how Norwegian Nils Gregoriusson Tveranger traveled to North America in the late 1800s to study shoemaking. Along the way he encountered and became enamored with the moccasins worn by the Iroquois tribe, which apparently made an enduring impression. More than thirty years later, after having established himself as a respected shoemaker back in Aurland, Norway, Tveranger introduced the “Aurland moccasin.” The initial design was a mashup of a moccasin and the traditional slip-on shoes from his hometown.

Thanks to the popularity amongst travelers from the United States and Europe, the style now renamed “Norwegian moccasins” began to be exported directly to those markets. It didn’t take long for them to find a loyal following and attract the attention of Esquire magazine which published a photo spread of Norwegian farmers wearing the shoes in a cattle loafing shed.

Inspired, American shoemaker G.H. Bass designed his own version, added a strip of leather with a cut-out pattern across the saddle and introduced the “Weejun.”

The rest, as they say, is history.

The second story tells us that sometime in the 1930s Raymond Lewis Wildsmith, shoemaker to the Royal Household of King George VI, created a pair of slip-on shoes for His Majesty to wear indoors. Some time after its initial appearance, the “Wildsmith Loafer” was adapted for outdoor use and the popularity of the style spread around the world.

Over the decades, the loafer seems to have defied logic by becoming the preferred style of a broad section of the population, including preppy college students, punk rockers, statesmen, businessmen, actors, pop-culture icons and the everyday guy.

How to Wear Penny Loafers

The penny loafer might be the most popular style of loafers for men. Originating from G.H. Bass, as noted above, this style features the signature diamond cut-out in the strip of leather along the shoes’ saddle.

This was a favorite shoe of college guys in the 1950s, especially what would come to be known as the “preppy.” Legend has it that they would slip a couple of copper pennies into the slot as both a fashion statement, and a practicality. Back then, a pay phone call cost two pennies and having them in reserve for emergencies was a smart move.

The penny loafer eventually migrated off of college campuses into mainstream life and caught the attention of Elvis Presley, JFK and other luminaries.

Our Roy Loafers and Cohen Loafers do justice to the original, with a modern taper and handsome profile, and are a great alternative to trainers or Derbies. Wear them with jeans, casual pants, chinos or shorts and you’ve got the makings of an attractive look that will get you noticed.

How to Wear Tassel Loafers

Even though still considered casual, tassel loafers step-up the formality quotient. And it makes sense, given the way they were created. 

In the late 1940s, Hungarian-American Paul Lukas, a debonair character actor, returned from Europe with something unusual: an Oxford with tassels dangling from the laces.

Lukas loved the idea, but preferred the shape and convenience of loafers to the Oxfords and asked several renowned American shoemakers to come up with something exciting based on the design he presented to them.

After much experimentation, trial and error, and brain power, one shoemaker succeeded in producing exactly what Lukas was after: the tassel loafer.

Gone was any trace of the original Oxford. The upper was now a wholecut piece of leather, with a distinct apron toe. Leather laces weaved through the topside and the entire construction was literally pulled together by the iconic tassels at the front.

You can see all of these gorgeous details in our Bernard Tassel Loafers which exude casual elegance. Perfect with a relaxed suit, dressy chinos or your nicest jeans, this shoe style will always look handsome and send the signal that you’re a confident dresser, as suave and sophisticated as the man who first wore them.

How to Wear Horsebit Loafers

Back in the 1950s, Guccio Gucci, a then fledgling shoe designer, combined the luxurious materials of full-grain leather with something so completely unexpected, some would say audacious, it was destined to become a success: a horse’s snaffle.

Reduced in size to fit across the saddle of the now popular loafer upper, the ornament shone like a beacon and signaled the rise of a new level of luxury. The horsebit loafer was born, and men’s fashion never looked back.

Even though the style is still quite popular, not many shoemakers actually make it. Our Beaumont Loafers are a mainstay of our collection, and the collection of many men. - including me. They are actually my most favorite pair of shoes.

There are some special details, such as the insole which is part of the upper. The true moccasin construction. And, of course, the individually molded, forged and polished solid brass horsebit adornment.

With a refined profile, the Beaumonts look stunning with tailored suits, wool trousers, fitted jeans and refined pants.

How to Wear Loafers Sockless or With Socks

To sock or not to sock, that is the question. At least that’s the question that’s been raging for decades when it comes to wearing loafers.

It’s a tough debate, with encampments on both sides, and some in the middle. What it comes down to is what your personal style dictates, what else you’re wearing, the weather and how your loafers are lined.

Now, if you choose to go with socks, you can always pair white and penny loafers like the Cohens, especially when wearing jeans. This is a classic combo that (I think) always looks cool.

Then consider socks which contrast subtly with the color and texture of your loafer. For example, a rich mustard yellow could look pretty fetching when slipped into a pair of brown suede Roy Loafers.

Or, you could go bolder and sport fire truck red socks, or rich burgundy with black Beaumont Loafers. Royal blue socks look killer with the dark brown or oak Beaumonts.

Patterned socks look great when donning a casual look, and dressy, sheer socks help to up the formality quotient when wearing Bernard Tassel Loafers and suits.

As far as the sockless look is concerned, let’s be frank, you always want to put your best foot forward and you have to consider how your ankles appear. That’s number one.

Secondly, if your feet tend to sweat a lot, be sure to either powder or spray them with an antiperspirant before slipping them into your shoes.

The third (or perhaps it should be first) consideration is the type of lining your loafer has. Ideally they will be fully lined with a material that lets your feet breathe, fights odor causing bacteria and regulates temperature. Fortunately, all Beckett Simonon shoes are lined with a wholecut piece of Vachetta leather which does all of those things, and adds an extra layer of comfort.

And, of course, be mindful of the weather. Going sockless isn’t a great idea if it’s raining heavily or if it’s terribly cold outside.

You could always wear a pair of no-show socks and still pull off the sockless look.

Conclusion

Now that you have all the information you need to help guide you through the wonderful world of loafers, go ahead and try out all of the exciting styles. Really, the possibilities are endless, just let yourself have fun and don’t worry about playing by “the rules.”

We’d love to hear about how you wear your loafers. Please send us a comment below.