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Home » Style » How to Style Penny Loafers

How to Style Penny Loafers

Updated: February 8, 2026 by David Em
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Penny loafers are slip-on shoes that have been around for a long time. They’re one of several types of loafers that are versatile and classy.

Penny loafer history

During the early 1900s, Nils Tveranger moved to Aurland, Norway, after learning how to make shoes in America. Nils developed the Aurlandskoen, also known as the Aurland Shoe.

This was the original penny loafer, which was inspired by the Native American mocassins hence the slip-on feature. During the 1930s, Norwegians visited America wearing the Aurland shoes, and they caught the attention of G.H. Bass, a footwear company founded in 1876 by George Henry Bass.

G.H. Bass saw it as an opportunity and created its own version called the Bass Weejun, which is short for Norwegian. This made them the first to market in America and became popular and the shoe of choice in the 1950s. Instead of being a plain loafer, G.H. Bass attached a strap across the top and created a slot for a small item, such as a penny.

Related: 9 best unstructured blazers

Black and brown Weejuns.
Black and brown Weejuns by G.H. Bass.

This was perfect because there weren’t any cell phones. Coins for a payphone could be hidden in a penny loafer in case of emergencies.

How to wear penny loafers

Penny loafers are versatile shoes that can be worn formally with a navy suit or casually with a t-shirt. The following are examples of what you can wear with penny loafers:

Blue jeans, white t-shirt, and brown suede penny loafers

Blue jeans, brown suede loafer, belt, and white t-shirt.
Photo courtesy of Nordstrom, Tod’s, and To Boot New York.

Khaki shorts, blue polo, and brown suede penny loafers

Khaki shorts, blue polo, brown suede penny loafer, and sunglasses.
Photo courtesy of Nordstrom and Tod’s.

Grey trousers, navy sport coat, and black leather penny loafers

Grey trousers, white dress shirt, navy sport coat, black belt and penny loafer.
Photo courtesy of Banana Republic, Nordstrom, and Eton.

Blue suit with brown penny loafers

Blue suit, tie, white dress shirt, and brown penny loafer.
Photo courtesy of Hugo Boss, Nordstrom, The Tie Bar, and Eton.

Cleaning and care

Keeping your loafers in good condition will ensure they last longer and that you look good wearing them. Whether you have suede or leather loafers, use a shoe tree to hold their shape and a shoe bag to avoid dust.

How to clean leather

Take the following steps to clean leather penny loafers:

  1. Remove dirt and debris using a soft shoe brush. Make sure you brush along the shoelaces and sole, as well.
  2. Add a small amount of soap into a bowl of water to create a cleaning mixture.
  3. Wet a clean cloth and wring out the liquid.
  4. Gently rub the surface of the loafer.
  5. With another clean cloth, wet it and wipe the surface to remove excess soap.
  6. Allow the loafer to completely dry in a cool area.
  7. Use baking soda or talcum powder to remove oil stains.
  8. Apply shoe polish to make it look new.

How to clean suede

Take the following steps to clean suede penny loafers:

  1. Use a suede brush to gently clean the surface of your loafer.
  2. Remove scuffs and marks with an eraser.
  3. Use white vinegar or rubbing alcohol on a cloth to clean tough stains.
  4. Protect your suede loafers with a suede protector spray.

Frequently asked questions

Are penny loafers comfortable?

Yes, penny loafers are comfortable slip-on shoes that can be worn with or without socks.

Are they formal?

They aren’t formal enough to be worn with a tuxedo. However, penny loafers work for anything in between going out on the weekend and a job interview.

Can I wear penny loafers in the winter?

Although they’re designed for warm weather, it’s possible to wear penny loafers in the winter. If you do, avoid wearing big and bulky coats because they’ll cause the loafers to look out of place.

Conclusion

Penny loafers are a must-have footwear item because they can be worn with many outfits and will keep you cool during warm weather. They’re timeless and fashionable shoes that’ll take any outfit to the next level.

Headshot of David Em.

David Em

Founding Editor

David Em is the Founding Editor of Next Level Gents, a men’s lifestyle blog. Since 2018, David’s mission has been about helping men build confidence through style, fitness, and grooming. He lives in Kansas City with his wife and daughter. He’s passionate about men’s fashion, cycling, and cooking.
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Headshot of David Em.
Hi, I’m David Em. I’m the Founder and Editor of Next Level Gents, a men’s lifestyle blog I started in 2018. I live in Kansas City with my wife and daughter. My goal is to share in-depth advice and tips to help you dress well and elevate your life. Learn More About Me

 

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