8 Best Penny Loafers for Men – Quality To Upgrade To In 2023


Everywhere you look these days, it’s loafers central. These casual dress shoes have made a comeback for the ages, and the best penny loafers for men are taking the fashion world by storm. Perfect for office shoes, nicer events, or preppy casual, penny loafers have been around since the 1930s and aren’t going anywhere anytime soon.

If you’re ready to upgrade your shoe game or fall in line with today’s latest trends, we’ve rounded up the top eight penny loafers for men that will transform any outfit from drab to dapper.

Key Takeaways

It’s indisputable: there are a lot of incredible pairs of loafers on the market. But as for the best penny loafers for men? After looking over dozens of sites and hundreds of reviews, we crown the Velasca Canoccial Penny Loafers king.

Crafted from soft Italian pebbled leather, they combine comfort and style. Sure, they’re a bit pricey, but they’re designed to be durable and long lasting, making them a worthy investment. If you’re looking for a pair that’s more budget friendly, the Cole Haan Pinch Penny Loafers are available on Amazon with a black leather construction and mocassin style toe.

Keep reading to discover the rest of our top choices for the best penny loafers for men.

Our Top Picks

wearing a pair of nostro penny loafers by velasca
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Velasca Canoccial Penny Loafers

Why They’re Great: There are penny loafers, and then there are the Canoccial penny loafers by Velasca. Italian made from pebbled calf leather, these shoes are supremely stylish and wonderfully versatile. They look as good with jeans as they do with suits and ties, suitable for the modern gentleman.

How They Feel: These shoes are more comfortable than your average men’s loafers due to the flexible sole and soft leather. Rather than rigid, these shoes are designed to move with you without falling apart after a year of wear. They’re also lightweight, making them an apt choice for travel.

Flaws But Not Dealbreakers: Purists may not like the tumbled look. Good thing these penny loafers also come in smooth black leather.

Material: Tumbled calf leather | Sizes Available: US 5 – 14 | Colors: 4

Dockers Colleague Penny Loafers

Why They’re Great: Dockers are workwear experts, and these penny loafers are a prime example. The perfect year round office shoes, these loafers are as classic as they come, with three colorways to choose from and a synthetic construction for a budget friendly price.

How They Feel: As some of the best penny loafers for men, these shoes are as comfortable as they are good looking. The cushioned footbed offers extra support for your commute, with a short break in period.

Flaws But Not Dealbreakers: Unlike most of the best men’s penny loafers, these are cut from man made materials rather than genuine leather. This may make them less durable than a high end pair.

Material: Synthetic materials | Sizes Available: US 7 – 13 | Colors: 3

Arterton Classic Loafers

Why They’re Great: Smooth as butter, these are the best penny loafers for casual wear. Made from German leather, they’re hand welted for extra comfort. In contrast, many loafers are Goodyear welted, which includes a cotton rib to anchor the uppers to the insoles. The benefit of a hand welted construction, as seen in these shoes, is the rib is carved by hand directly into the insole. This makes for stronger, more comfortable, and lighter loafers than those with a cotton rib.

How They Feel: Complete with hand stitching and leather soles, these penny loafers are lightweight and comfortable. Choose between a standard or wide width, and even upgrade the soles with topy (rubber) or triumph toe plates if you need some extra durability.

Flaws But Not Dealbreakers: Given the artisanal nature of these shoes, they’re a slightly higher price point than many of the best men’s penny loafers. But totally worth the splurge.

Material: Leather | Sizes Available: UK 7 – 12 | Colors: 2

Myrqvist Stenhammar Penny Loafers

Why They’re Great: Suede penny loafers scream distinguished and classy. Great for office or dressy wear, this pair from Myrqvist embodies fine Portuguese craftsmanship and premium British materials. They feature a half rubber sole for a slim silhouette while still accommodating a wider foot.

How They Feel: One of the best aspects of these penny loafers is there’s little to no break in period. Expect them to be comfortable right out of the box. And while they’re plenty malleable, they retain their shape well, making them a long lasting footwear investment.

Flaws But Not Dealbreakers: Some reviewers state that the shoes are pretty squeaky, especially on wooden floors.

Material: Suede | Sizes Available: US 5.5 – 13 | Colors: 6

Oliver Cabell Mono Penny Loafers

Why They’re Great: Live out your Italian mobster dreams with these Oliver Cabell penny loafers. Suitable for the Sopranos and, dare I say, the Godfather himself, these black and white shoes are an incredible statement piece for a monochrome outfit. Aside from the unique colorway, we love these Portuguese-made shoes for daily use or as summer loafers, ideal for resort wear and outdoor weddings.

How They Feel: Crafted from Italian leather, these penny loafers are designed with comfort in mind. They’re thoughtfully lined with a softer leather over a foamy footbed to aid in support and all day ease of wear.

Flaws But Not Dealbreakers: If you’re going for a more pared back look with your penny loafers, this two toned pair may not cut it.

Material: Full grain leather | Sizes Available: US 6 – 14 | Colors: 1

Cole Haan Pinch Penny Loafers

Why They’re Great: I feel like sometimes, when you’ve seen one penny loafer, you’ve seen them all, which is why this Cole Haan pair is so attractive. Outfitted with pinched leather around the toes, they have a dressy moccasin feel. Finished with a stacked heel that won’t wear down any time soon, these durable penny loafers are some of the best on the market.

How They Feel: Aside from the sleek look, these penny loafers have responsive cushioning in the footbed for added comfort and to propel you forward. Coupled with extra traction on the soles, these shoes will get you where you need to go.

Flaws But Not Dealbreakers: Thanks to the pinched toe, these shoes don’t have the classic penny loafer look. A flaw for some, a win for others… your choice.

Material: Leather | Sizes Available: US 6 – 16 | Colors: 2

G.H. Bass & Co. Weejun 90 Larson Penny Loafers

Why They’re Great: When it comes to designer penny loafers, this pair from G.H. Bass & Co. gets you the most bang for your buck. They’re $250 but look like a million dollars, with a trendy sole that’s slightly chunkier than normal and a mix of leather and suede for some interesting contrast.

How They Feel: While it may take some time to break them in, these penny loafers are super comfortable and soft on the feet. The thicker soles aid in support, and the treads make them suitable for year round wear – no one’s slipping on ice with these babies.

Flaws But Not Dealbreakers: Chunky soles can throw some people off, but haven’t you heard? They’re all the rage these days.

Material: Leather | Sizes Available: UK 5 – 12 | Colors: 3

Common Projects Leather Penny Loafers

Why They’re Great: As far as streetwear goes, these Common Projects penny loafers have been on the scene for quite a while. They’re as timeless as they are modern, with the brand’s serial number stamped onto the side. Made in Italy from the finest materials, these penny loafers will never go out of style despite the trendy semi-platform sole.

How They Feel: These penny loafers feel good on the feet, especially given the extra traction on the soles. The thicker soles also provide more support than the classic half rubber sole seen on most pairs of penny loafers for men.

Flaws But Not Dealbreakers: The sole on these penny loafers is distinctly chunky, which is a turn off for some guys. They also have a luxury price tag to match the luxury offering.

Material: Leather | Sizes Available: EU 40 – 47 | Colors: 1

wearing a pair of lysekil penny loafers by myrqvist
myrqvist / Instagram

Buying Considerations for the Best Penny Loafers


One of the most important considerations when choosing penny loafers for men is the material. Typically, penny loafers are made from leather, suede, or synthetic materials. Aside from how they look, the material affects the durability of the shoe, with leather and suede being the most enduring, while synthetic materials have a much shorter lifespan.

For year round penny loafers, opt for leather, which can withstand the seasons. Suede is great for drier months like summer and autumn, and choose synthetics if you’re on a tight budget. However, if you consider footwear to be an investment, it’s worth splurging on a high end leather construction that will last for years to come.


It’s also worth thinking about the color of your loafers to know what you can wear them with. Black loafers are great office shoes that work well with dark suits and a range of deeper colors. Black penny loafers are some of the most classic and are a dependable option with pretty much any getup.

On the other hand, brown loafers make a statement, especially when worn with lighter, creamy colorways. Brown penny loafers are easy to dress down and look great with jeans, khakis, and chinos. This makes them a more versatile, casual option than black leather loafers.

And if you’re not afraid to stand out from the crowd, express your individuality with colored loafers. Choose a two toned pair to lean into a jazzy look, or go for burgundy penny loafers for something a bit different but still easy to style.


The price of loafers is determined mainly by the material and construction of the shoe. Materials like leather and suede are more expensive but will last much longer than loafers made from cheap synthetic materials. If you plan on getting a lot of wear out of your loafers, it’s worth spending a bit more so they’ll last for years rather than falling apart after a few spins around the block.

wearing a pair of Sfoderato penny loafers by velasca
velascamilano / Instagram

Why You Should Trust Us

As something of a globetrotting trend hunter, I’m always on the lookout for the latest crazes in men’s fashion. After spending the past six months between Paris, New York, and London, I’ve seen one constant in the guy’s footwear department: penny loafers.

Inspired by the fashionable men I’ve come across recently, I’ve dug deep into the world of penny loafers, learning the history of the shoe, along with the best brands and materials to choose from. Rounded up in this article, I hope it helps any guy looking to enhance his style with a pair of the trendiest shoes on the market today, and what I’m confident will be for years to come.

Final Verdict

The best men’s penny loafers are some of the most versatile shoes a guy can have in his closet. If you’re looking to invest in a durable pair that will go with anything, the Velasca Canoccial Penny Loafers are a stellar choice with unique pebbled leather and a soft construction. However, if you don’t want to spend an arm and a leg on a pair of shoes, the Cole Haan Pinch Penny Loafers are a safe bet that are easy to dress up or wear with more low key outfits.


    • Penny loafers are a casual type dress shoe traditionally made from leather or suede with a rounded toe and, typically, a leather sole. Unlike tassel loafers, a strap crosses the upper of penny loafers with a small slit in it, which is how you can distinguish penny loafers from other kinds. Penny loafers can be worn with or without socks for men and are a type of shoe every man needs.

      • Penny loafers are a type of loafer that get their name from the strap across the top of the shoe that includes a small slit, roughly the size of a penny. When the shoes were first introduced in the 1930s, this slit was a convenient place to stash change for payphones and is still used in the shoe design today.

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