The Best Penny Loafers of 2023

By Cory Maki Cory Maki has been verified by Muck Rack's editorial team
Published on February 15, 2023

Penny loafers are a classic shoe that has transcended time and remained one of the most popular shoes around. They are also versatile shoes, with the ability to be designed and worn for a number of occasions, from casual lounging to formal events and the workplace. Read on to see all the different kinds of penny loafers out there.

If you’re in a hurry, here are our top 3 quick picks for the Best Penny Loafers:

Criteria for Choosing the Best Penny Loafers

While penny loafers have a few classic details that stay pretty much the same, there is a lot of variety around the rest of the shoe. To pick some of the best penny loafers out there, the key was to select high-quality shoes that demonstrate the various forms and unique qualities of a penny loafer. Here are a few of the things that were considered:

  • Comfort: Dress shoes do not have to be uncomfortable, and that goes double for penny loafers. Penny loafers are laceless shoes, so being able to slip them on and off is a given. They can even get so comfortable that they feel like classy slippers. Things like arch support and cushioning, as well as fit, were considered.
  • Style: The style of penny loafers is also important. Whether you want something casual or formal, the iconic front saddle should stand out, and the rest of the shoe should have the same elegance and style one would expect. There are exceptions with the more casual versions, but even they can have style.
  • Quality: At the end of the day, these are meant to be high-quality shoes, from the material used to the heels and insoles. The shoes on this list were chosen for that very reason, with each of them being durable and high-quality shoes. After all, there is no point in buying an expensive pair of dress shoes that will not last.

There are some other factors that played a role as well, such as the sizes and colors available. Additionally, the price of the shoes and their purpose influenced whether they made the list.

The 7 Best Penny Loafers

There are a lot of brands out there that sell penny loafers, but there is also a lot of low-quality, uncomfortable shoes on the market that are not worth your time or your money. It is important to find a pair of shoes that not only look good but feel good, and that is where this list comes in. Below are some great shoes that stand above the rest.

Rockport Men’s Classic Penny Loafer

If you are looking for a pair of high-quality but affordable penny loafers, Rockport is a brand you have to check out. Their classic penny loafer is made using 100% leather that will last and look great the entire time. This shoe also has a classic, stylish look that makes it an upscale choice that suits a variety of occasions.

The heels on these shoes are around 1”, and the sole is synthetic. Additionally, the shoe is designed to be a mix of stylish and comfortable, so you do not have to worry about stiff leather or narrow sides. In fact, this shoe comes in a variety of sizes, including wide versions. There is even added cushioning for comfort and shock absorption in the heel.

  • It is made from 100% genuine leather
  • The material makes it easy to clean and maintain
  • The design and style are ideal for almost all situations
  • There are numerous sizes, including wide versions
  • They focus on comfort along with style

  • The sole makes the shoe a bit slippery
  • They do not provide as much arch support as they could

Nunn Bush Men’s Drexel Penny Loafer

Another great penny loafer made from 100% genuine leather comes from Nunn Bush, a brand that has been making remarkable dress shoes for a long time. They are a reliable brand that seeks a balance between looks and comfort, and they definitely accomplish that with this shoe, which features a stylish, classic appearance for any occasion.

This shoe can be purchased in a variety of classic colors that focus on browns and blacks. It also comes in many sizes, ranging from 7 to 14, with some wide options being available as well. Looks aside, the real selling point of this shoe is comfort. It has a padded sock lining with memory foam and comfort gel, ensuring comfort in every step.

  • The material used is 100% genuine leather
  • There are a range of colors and sizes available
  • The Kore Comfort Technology ensures a comfortable fit
  • The style is classic and is suitable for many occasions
  • The soles provide great traction

  • Some people find the leather stiff at first

Cole Haan Men’s Howland Penny Loafer

If treading the line between upscale and casual is your thing, then this penny loafer from Cole Haan might be right up your alley. The material is 100% genuine leather, which is always nice, but it has a vintage finish that gives it a fantastic look. It also has moccasin stitching and a split sole without much of a heel, which is great for driving and mobility.

Although the overall design does not lend itself as well to formal occasions, it still has an air of elegance around it. The shoe comes in a few different colors, including the saddle tan featured here. However, it is more suitable for people with narrow feet. So if you are looking for a comfortable, classic loafer that still has a bit of style, consider this loafer.

  • The shoe is made with 100% genuine leather
  • It is a more casual penny loafer that retains some formal style
  • The low heel and overall design make it more maneuverable
  • It is a durable shoe that will last

  • They are not as good for those with wide feet
  • The sizing might run a bit small

Cole Haan Men’s Grand Atlantic Penny Loafer

Cole Haan sells numerous types of loafers, from comfortable and casual to those perfect for formal occasions. But the shoe featured here remains firmly in the casual category, with a focus on comfort and traction over everything else. To start, this shoe can be purchased in leather or nubuck, and it comes in a range of blacks and browns.

Once again, the sole is where this shoe stands out. It has a classic look, but the sole is solid and made from a combination of lightweight EVA and rubber pods. The material makes this shoe comfortable and easy to move around in while ensuring that it does not lose out in traction. There is a padded sock lining for even more comfort as well.

  • This more casual penny loafer still has a versatile look for many occasions
  • The material comes in high-quality leather or nubuck
  • The sole is made to be both lightweight and functional
  • There is a padded sock lining for increased comfort

  • It seems that the shoe runs small for many people

STACY ADAMS Men’s Pierce Moe-Toe Slip-on Penny Loafer

Penny loafers have a classic look that includes a laceless design and a saddle that sits horizontally across the top. While that saddle is typically leather, that is not always the case, such as with this snazzy loafer from Stacy Adams. It is made from 100% leather, but the front features braided loops with a metal ornament that adds some uniqueness.

The shoe comes in two colors: black and cognac. But the metal ornament is silver on both. You can also get the shoe in any size between 7 and 15, making it easy to find a suitable size. They are designed with comfort in mind as well. The insole is cushioned with memory foam, adding support and shock absorption, and the lining is breathable.

  • The metal ornament adds a touch of uniqueness to this penny loafer
  • The material is 100% leather, and the soles are high-quality as well
  • The memory-foam insole provides support and shock absorption
  • There is a leather lining that improves comfort and breathability

  • The paint on the metal ornament is not the highest quality

SWIMS Men’s Slip-On Washable Penny Loafers

Penny loafers do not have to be a formal shoe, a fact shown by some of the pairs already seen above. However, this slip-on penny loafer from SWIMS takes things in an entirely different direction. The material and design of this shoe are meant for one thing: functionality. It all starts with the material, which is a mix of fabric, mesh, and rubber.

The material gives this shoe the ability to get wet without being ruined, meaning they can be used around water or day to day without a problem. The shoe is also ventilated and flexible, allowing your feet to breathe and giving you more mobility than your average penny loafer. You can even toss them in the washing machine if they get dirty.

  • The design makes them a great day to day casual shoe
  • They are water-friendly and machine washable
  • There is ample ventilation, ensuring maximum breathability
  • The sole is flexible and makes the shoe easy to move in
  • When worn as a casual shoe, the appearance is fantastic

  • They cannot be used in a formal occasion whatsoever

Dockers Mens Colleague Dress Penny Loafer Shoe

If you want a classic, elegant shoe at a great price, Dockers offers a penny loafer that is sure to please. There are some detracting factors with this loafer, but for the price, you get comfort and quality that is well worth it. In fact, it is one of the more comfortable options out there, with a cushioned footbed and great support. The fit is nice as well.

The details are what fall a bit short with this shoe. There are only two colors, which are tan and black, and the sizes only range from 7 to 13. The material is 100% synthetic as well, which likely means the shoe will not last as long as one made with genuine leather. Additionally, while the rubber sole gives plenty of traction, it is not all that durable.

  • The shoe has a classic look at a low price
  • There is plenty of support and cushioning for a comfortable wear
  • The rubber sole provides plenty of traction

  • The material is 100% synthetic and will not hold up as well as leather
  • There are not many color and size options

How to Shop for Penny Loafers

As you might have figured out from the list above, there are a lot of different penny loafers out there. While penny loafers are only a type of loafer, there are also a number of distinctive penny loafers, which range from casual shoes to formal shoes. While it might make it difficult to find the best pair for you, considering these things will help:

  • Occasion: Where and when do you plan to wear your penny loafers? If you are going for a more casual look, then you can wear just about anything, all the way down to penny moccasins. However, for more formal occasions, you will want smooth leather penny loafers or calf penny slip-ons.
  • Color: When you are looking for a pair of penny loafers, consider what would go best with your wardrobe. Of course, if you are wearing them casually, you can go with almost any color, even something unconventional, but browns and blacks work best in formal settings.
  • Comfort: It cannot be stressed enough how important comfort is, especially if you plan to wear your penny loafers regularly, even daily. You want a pair of shoes that you can walk around in without ending up with sore feet.

There are plenty of other considerations, such as things like price, the heel, and the overall style and appearance, but all of that will become far easier to figure out once you take care of the things above.

In Conclusion 

Penny loafers are a great type of shoe. Not only are they seemingly timeless, but they can work for a multitude of occasions. You can even use certain pairs of high-quality slippers. Just make sure you keep where and when you will be wearing them in mind when looking for a pair. It can make a big difference.

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By Cory Maki Cory Maki has been verified by Muck Rack's editorial team

Cory Maki is a former Staff Editor and the Business Development Manager at Grit Daily.

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