The Eternally Fabulous Penny Loafers: Your "Go To" Shoes

A guide to penny loafers

Is there any shoe as timeless, stylish, and versatile as the classic penny loafer? Since their creation in the 1930s, penny loafers have been a go-to shoe for style icons from President John F. Kennedy to Cindy Crawford. 

Despite their wide-ranging appeal, penny loafers are a distinctly preppy fashion staple. They're able to add a bit of classic preppy charm to just about any outfit. 

But how did penny loafers become such a must-have fashion item? Read on to learn more about the history of penny loafers and why you should have at least one pair in your closet. 

The History of Penny Loafers

Penny loafers were first created in Norway in the 1930s by a Norwegian shoemaker named Nils Gregoriusson Tveranger. Tveranger was inspired by the moccasins of Native Americans and the simple slip-on shoes of Norwegian fisherman.

The design became popular in Europe and the United States, and in 1934, G.H. Bass created the iconic Weejun loafer. The name "Weejun" is a play on the word "Norwegian". 

To give them a distinctive style, The Weejun loafers featured a leather strip with a cutout on the saddle of the shoe. This cutout happened to be the perfect size for a coin. It soon became the style to wear a penny in this cutout, that's how the penny loafer was born.

Penny loafers became very popular in the 1950s and 1960s. They were popularized by James Dean, JFK, and masses of Ivy League students. Since then, penny loafers have found fans everywhere from London punks to the high fashion runway.

How to Wear Penny Loafers

The better question might be, how can't you wear penny loafers? Penny loafers work well with so many different types of outfits. Their versatility is one of the things that make penny loafers such great shoes. 

When pairing penny loafers with an ensemble, the trick is to choose the right type of penny loafers for the occasion. Some styles of penny loafers are more formal than others.

Leather is a material that works well for many occasions, but the color and styling may vary. Suede is a nice option for a unique yet laidback look. 

Subtle details on your penny loafers can have a huge effect. Luxurious stitching and high-shine leather will make a pair of penny loafers suitable for fancy dress. 

Want a little more inspiration on how to wear penny loafers? Here are some penny loafer outfit ideas to get you started. 

Everyday Wear

Penny loafers are a great option for your new daily shoe. They're chic but still comfortable enough to replace your beloved sneakers. 

Men and women alike can wear penny loafers with jeans or casual pants and a button-down shirt for an instantly laidback yet polished look. During colder months, add a classic knit sweater for cozy charm. 

For the Office

Penny loafers are also a perfect shoe for the office. They're business casual and comfortable.

For men, a pair of penny loafers looks great with chinos and a collared shirt. Women can go for a similar look or opt for a skirt or dress instead. 

Dressed Up

Depending on the style and material of your penny loafers, they can also work for more formal occasions. For semi-formal occasions, you can have a bit of fun with your penny loafer style. Consider unusual colors or patterns that complement your ensemble. 

For formal outfits, go with shiny leather loafers that are either sleek or have elegant detailing. Choose black or another appropriate neutral color to keep your outfit looking sophisticated. 

Men's Penny Loafers

Looking to add a new pair of penny loafers to your wardrobe? Penny loafers are a great complement to so many outfits for men.

There are many styles of penny loafers out there, but you can't go wrong with the classics. Here are a few of the best timeless penny loafer styles for men. 

G.H. Bass Logan Weejuns

If you're looking for the ultimate classic penny loafer, look no further. These Logan Weejuns feature smooth leather in classic black with just the right amount of shine. 

The iconic styling adds a little pop of detail, and the padded arch support ensures you'll be comfortable and stylish. 

Cole Haan Howland Penny Loafer

If you're looking for something more laidback but still sophisticated, these penny loafers feature soft pebbled uppers and are a great shoe for casual occasions. The tan calfskin is the perfect complement for your favorite jeans. 

Women's Penny Loafers

Since their creation in the 1930s, the definition of "penny loafer" has expanded to include design elements like animal prints and towering heels. While there's a time and a place for these modern designs, we have a soft spot for the classics.

Jack Rogers Quinn Penny Loafers 

Our favorite women's penny loafers embody everything we love about the classic style while adding just a little unique charm. These timeless black loafers feature a delicate scalloped edge for just the right amount of flair.

The slight heel gives just enough lift and plenty of comfort. The durable leather construction is sophisticated and ensures these shoes will be a favorite for years to come. 

Put Some Prep in Your Step with Timeless Penny Loafers

Penny loafers are a classic shoe that has been a fashion staple ever since their invention in the 1930s. Their effortless preppy style brings a bit of sophistication to any outfit, whether you wear them with your favorite jeans or a summer suit.

Looking for more ideas about how to incorporate classic preppy fashion into your modern wardrobe? Check out our blog for more style tips.  


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