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What are Penny Loafers? Ways to Style this Classic Type of Shoes

Footwear plays a bigger role in your outfits and overall aesthetics than you might initially realize. Wearing the wrong shoes can ruin the look of even the most well-crafted outfits. Similarly, rocking a pair of high-quality shoes can drag an okay outfit out of mediocrity.

Among a large number of unique types of boots and shoes available to men, only a few are able to transcend their niche and gain the status of a must-have. Penny loafers are one of these legendary pairs of shoes, and this guide will give you the answer to “What are penny loafers? How did they gain this much popularity? How can you style them successfully today?”

Let’s get started.

History of Penny Loafers

The answer to “what are penny loafers?” wasn’t always what it is today.

Penny loafer origin is around the 1900s. Back then, a certain Norwegian man decided to improve the design of the teser, which was a traditional laced shoe worn by fishermen and farmers. The man, named Nils Tveranger, studied in America and returned to his homeland to complete the design. The first iteration was a mix between traditional teser and Iroquois Native Americans’ moccasins.

By 1936, the design was in America thanks to John Bass, the son of the founder of the American footwear label G.H. Bass. The label made some changes and the definition of “what are penny loafers” started to change alongside them.

These leather shoes became the big new thing in the 1960s, with even the biggest celebrities wearing them. It didn’t take long after that for these to become a permanent part of business professional attire either with slight design iterations as 80s penny loafers and 90s penny loafer.

Penny Loafers Style

The past of penny loafers, moccasin loafers, and penny loafers 80s style, although fascinating, is not very relevant anymore. What matters today isn’t “what are penny loafers,” rather what you can do with them.

Integrating these shoes into your daily life is both easy and tough. Easy because they’re not that picky when it comes to outfits. Everything from casual everyday ensembles to casual interview outfits is equally welcome. Tough because you have to spend some time and effort in finding outfits that bring out the true potential of these shoes.

Lucky for you, we already did the hard work. Here are a few of the most notable penny loafer outfits for men.

Penny Loafers with a Suit

Penny Loafers with a Suit

The simplest penny loafers matchup is also the most effective, suit with loafers. To say that this combo works together flawlessly would be an understatement. The suit makes these slip-on penny loafers look mature and professional, while the loafers make the suit outfit a bit less intense.

If you’re worried about matching the right color, just go for black or neutral 90s penny loafers. They work well with almost any suit you can think of. That said, if the suit color allows, there is nothing that beats the charm of brown or tan leather penny loafers.

Casual Penny Loafers

Casual Penny Loafers

What are penny loafers best suited for? The answer to this is not clear. In other words, you can wear them with casual clothes as well. A prime example of their casual potential would be with a white shirt outfit. All you need is a white crew neck t-shirt, a pair of blue straight-cut jeans and brown penny loafers.

Without the loafers, this outfit is nothing more than the simplest attire a man can put on. But all you have to do is add these shoes, and the entire outfit starts looking well thought-out and prepared.

Preppy Casual

Preppy Casual

The casual side of penny loafers is much more exciting than it seems at first. Sure, they can enhance the looks of a simple two-piece ensemble, but they can also be a meaningful addition to a proper preppy outfit.

A great outfit that proves this statement features a pair of black chinos, a light grey button-up and a dark brown sleeveless sweater. All in all, a pretty dapper combo. Now add in brown and white penny loafers, and this preppy outfit is ready to be in a fashion magazine. Also, the ideal brown shoes with black pants combo play some part in making this outfit a success as well.

Monochrome Outfit

Monochrome Outfit

All black or an all white outfit for men are a strange yet fascinating aspect of fashion. They are quite difficult to pull off successfully, especially without getting too bland to look at. But you can avoid the issue altogether with a pair of penny loafers.

What are penny loafers doing in an all-black or all-white outfit? The answer is simply adding variety and making the otherwise boring outfits more interesting. Also, wearing black penny loafers under an all-black outfit will also achieve the goal of making the final outfit more interesting.

With a Leather Jacket

With a Leather Jacket

The combo of these shoes with leather jackets works so well that you’ll ask yourself, what are penny loafers not good at? This outfit looks its best when you match the leather jacket with similar leather penny loafers.

A fine example of such an outfit would start with a pair of blue jeans with a light blue button-up. The shirt will be topped by a brown bomber jacket, while the jeans will get capped by a pair of brown penny loafers for men with a similar shade. This style makes pretty good graduation outfits as well.


When were penny loafers popular?

The popularity of penny loafers originals peaked around the 1950s and 60s. At that time, everyone from athletes and major celebrities to even the US president was wearing these.

Why are they called penny loafers?

The slot on top of penny loafers was wide enough to house a single penny in each shoe. Though dress penny loafers with penny slots are phasing out of style. 

Are penny loafers in style?

In short, yes. Penny loafers are still plenty popular for business casual, everyday casual, and preppy styles. They also make excellent matchups with men’s vacation outfits.

Final Words

What are penny loafers? Are they formal, or are they casual? Do they work with any outfit, or are there special penny loafer outfits that look incredible? The answer is simply all of the above. Penny loafers are a must-have for any man looking to make a lasting impression with his footwear choice. 

And for those seeking a touch of sophistication, consider upgrading to custom leather loafers. Crafted with precision and style, they elevate any ensemble with timeless elegance.

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