Penny Loafers with Penny — History and Review

Penny Loafers with Penny

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:  Top 5 Men's Shoes for Heel Pain When Walking

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.

Penny loafer definition
A penny loafer

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:  Top 10 Men’s Dress Shoe Brands

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.

Wearing a loafer with shorts
Source: DMarge

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:  Shoe Reps - Everything to know before buying

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.

Wearing a penny loafer in winter


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!

Leave a Comment

Your email address will not be published. Required fields are marked * Protection Status