Penny Loafers with Penny — History and Review | (2024)

Men's Shoe / By Dominic Ogodo

Penny Loafers with Penny — History and Review | (1)

The history of penny loafers is traced back to Norwegian farmers and fishermen in the early 1900s.

It was therefore introduced in the American fashion culture when some American students traveling to Scandinavia saw the simple style and decided to take it home.

So, between 1934 and 1936, G. H. Bass, (an American footwear brand) made the first penny loafer. The company popularized the new style with their “Weejun” loafer.

The name “Weejun” is coined from “Nor’wegian'” in regard to the origin of the style (Norwegians).

The Weejun by Bass came with a unique style: a strip of leather running horizontally across the vamp. On this leather is a cutout, enough to hold a round object like a penny.

Why the name Penny Loafers?

Over time, the shoe style became popular among prep school students.

They gave the loafer the name “penny loafer” because they could insert a penny (coin) in slit of the leather embellishment crested on the shoe.

Then a phone call was just a penny. So, you could say it was an alternative for a purse.

Therefore, having a penny loafer with a penny in it is as good as buying the loafer style and inserting the penny coin yourself.

Read Also: Best 20 Men's High-quality Dress Shoes Under $50

What is a Penny Loafer?

A penny loafer is a style of loafer that features a strip of leather called saddle across the vamp.

On the saddle is a diamond-shaped cutout where users were believed to insert a Penny. It is from this action that the name “Penny Loafer” was coined.

Just like every other loafer, a penny loafer is a slip-on and has a relatively low heel and a mocassin-like seam along the vamp. Some have a flat sole while others feature a thicker sole.

Those with flat soles have either a glue construction or Blake welt. A penny loafer with a thicker sole like oxford and derby is likely to have the Goodyear welt construction.

Obviously, those with goodyear welt are best followed by those with blake welt. We do not recommend cemented or glued shoes.

Read Also:Crocs Shoes Review: History, Design, Pros and Cons

Penny loafer vs tassel loafer: what’s their difference?

A leather strip called saddle runs horizontally across the vamp in penny loafers, while in tassel loafers, decorative leather laces are attached to the vamp such that they dangle.

Do you wear penny loafers with socks?

Yes, you should wear your loafers with no-show socks for hygiene and comfort sake. Wearing a loafer exposes your ankle, and that’s the style. So do not wear full or half socks.

Can penny loafers be worn with a suit?

Loafers generally are casual shoes and wouldn’t go down well with a suit (in a business or formal setting). Instead, go for oxford or derby.

Read Also: How to Wash Hey Dude Shoes - Super Easy Guide

Nevertheless, modern fashion might say otherwise. People wear penny loafers on a suit and still fall in line to look smart. If you wish to consider this, go for a black penny loafer or tassel loafer.

Are penny loafers in style in 2021?

Penny loafer is a timeless style that has existed for years. According to Gentlemen Gazette, penny loafers is the most popular style of loafer in America. This growth in popularity is a positive sign that it is a style for today and tomorrow.

Can you wear penny loafers with shorts?

The cool thing about fashion is that you’re free to try out so many styles because there are no rigid rules. Nothing stops you from wearing a pair of shorts with a penny loafer. Perhaps it’s summer or a casual party with friends and you just want to look simple.

However, we suggest you go with shorts that are a bit above the knee and a tailored shirt.

You can also wear penny loafers with a tuxedo, jeans, chinos, and a blazer.

Are penny loafers formal or casual?

Originally, penny loafers are casual shoes but over time, they’ve transcended into the business and formal class.

Tassel loafers are seen to be more formal than penny loafers anyway. But a black penny loafer is more formal than a pink or yellow tassel loafer. Do you get the point?

Read Also: Best Non-Slip McDonalds Shoes For Employees

Can I wear a penny loafer in winter?

You don’t have to keep your loafers behind the closet because it’s winter. You might just need to do something different to rock it on.

To wear your penny loafers in winter,

  • Get yourself a pair of thick woolen socks. Ensure it is the same (or close to) shade of color as your shoe.
  • Your trousers should be a bit longer in the leg than they would be in summer.
  • Lastly, a chunky heel and thick rubber-soled loafer would serve best.


Penny loafers are characterized by a strip of leather running horizontally across the vamp. On this leather embellishment, is a cutout shaped like a diamond.

Weejun by G. H Bass is the first brand of this style. When Weejun became common among preppy students, they gave it the name penny loafer since they could slide in one or two pennies in the leather slit of the shoe.

Although it is generally seen as a casual shoe, penny loafers are sometimes worn to formal and business events. It is a style that has come to stay. Consider getting a few pairs into your shoe closet (if you don’t already have).

Related Posts

Top 10 Chukka Boot Brands You Should Go For

Best 20 Men’s High-quality Dress Shoes Under $50

15 Brown Monk Strap Dress Shoes for Men

Proven Ways on How to Waterproof Your Snow Boots

14 Benefits of Leather Soles Over Rubber and Plastic Soles

Please Share. Thanks!

Penny Loafers with Penny — History and Review | (2024)


Should you put pennies in penny loafers? ›

Placing a penny in the loafer's slot became a popular way to customize the shoes and differentiate themselves from others. Beyond the aesthetic appeal, the act of inserting a penny holds symbolic meaning for some individuals, representing good luck or a reminder of the value of money.

Why did people put a penny in penny loafers? ›

Around the '50s, American college kids only had the phone lines available for emergency calls, hence the need to always have two cents on hand, the cost of a call. With the risk of losing the coins in the pockets, the safest place was the slot of the Weejuns, which began to be called Penny Loafers.

Who makes the original penny loafers? ›

In 1936 Bass became aware of European interest in or at Norwegian slipper type moccasin and developed a similar product for the American market. Christened Weejuns it was an instant success that has stood the test of time. Share: We're celebrating 85 years since George Henry Bass created the iconic Penny Loafer.

Does anyone still wear penny loafers? ›

Why penny loafers deserve a place in your wardrobe. While the penny won't get you very far these days, the style has stood the test of time – and for good reason. The shoe is a great addition to your wardrobe – wear it instead of sneakers with jeans or chinos, or instead of a dress shoe with summer-weight suits.

Is it OK to wear penny loafers with jeans? ›

Penny loafers

Their leather construction exudes refinement, elevating the overall look while ensuring comfort. Penny loafers with jeans epitomize a fusion of style and ease, making them a go-to choice for the modern man.

When did people start putting pennies in loafers? ›

In 1950s America before trainers were invented, the Weejun became the shoe of choice for young men and students. It became fashionable to keep a dime in the half moon cut out slot of the leather strip. This eventually gave the shoes their colloquial name of Penny Loafer, which is still used today.

Are penny loafers making a comeback? ›

Timeless designs like penny loafers, ballet flats, and brogues are making a comeback, but with a modern twist. Expect to see these traditional silhouettes in unexpected textures and colors, blending the old with the new in a way that's uniquely 2024. The demand for comfort shows no signs of slowing down.

What's the difference between penny loafers and loafers? ›

The Penny loafers are distinct not only because of the easy, slip on feature but because the design includes a horizontal strap across the vamp or front area of the shoe. The leather strap includes a small center opening, which is the perfect size to slip in a small round object like a coin or specifically, a penny.

How do you look good in penny loafers? ›

For casual occasions, you can pair penny loafers with jeans, chinos, shorts, and a casual shirt or t-shirt. This look is perfect for a weekend brunch or a casual evening out. For a more formal occasion, penny loafers can be paired with dress pants, a blazer or a suit, and a dress shirt.

What is another name for penny loafers? ›

Slip-ons are typically low, lace-less shoes. The style which is most commonly seen, known as a loafer, slippers, or penny loafers in American culture, has a moccasin construction.

What is the meaning of Weejuns? ›

The Weejun, the shoe that would ultimately define the brand, was introduced in 1936. Inspired by the traditional Norwegian Aurland shoe, George Henry Bass reimagined the design by adding a strap across the front with a diamond-shaped cutout, which resembled a slot for a penny.

What is the most versatile penny loafer color? ›

Brown is your best bet if versatility is what you're aiming for. A medium shade of brown specifically can transition smoothly from day to night, from casual outings to business meetings. Pair them with jeans, chinos, or even suits - brown loafers seldom disappoint.

What do penny loafers say about you? ›

Penny Loafers

A great pair of loafers says to everyone that you are stylish, adaptable, and can fit in anywhere.

Are penny loafers in style 2024? ›

Penny loafers are the most versatile pair of shoes to have in your rotation and can be worn in fully suited up settings or even shorts. They're the perfect shoe to have this season.

Why do people put pennies in their shoe? ›

Carrying the coin into her wedding day was thought to attract wealth and it was believed to be most effective if it was placed in the shoe by her father. Since sixpence coins no longer exist, today's brides often substitute a penny for this tradition.

How do I keep my penny loafers from slipping? ›

Opt for socks with grips: Many socks have rubber grips on the bottom, providing additional traction inside your shoes. Choose moisture-wicking materials: Socks made from materials like merino wool or synthetic fibers can wick away moisture, preventing your feet from sliding around in your loafers.

Top Articles
Latest Posts
Article information

Author: Sen. Emmett Berge

Last Updated:

Views: 6285

Rating: 5 / 5 (80 voted)

Reviews: 95% of readers found this page helpful

Author information

Name: Sen. Emmett Berge

Birthday: 1993-06-17

Address: 787 Elvis Divide, Port Brice, OH 24507-6802

Phone: +9779049645255

Job: Senior Healthcare Specialist

Hobby: Cycling, Model building, Kitesurfing, Origami, Lapidary, Dance, Basketball

Introduction: My name is Sen. Emmett Berge, I am a funny, vast, charming, courageous, enthusiastic, jolly, famous person who loves writing and wants to share my knowledge and understanding with you.