5 Best Penny Loafers for Men: Unmatched Adaptability

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by  Karlton Miko Tyack | Last Updated: 
best penny loafers

Yes, they’ve gone in and out of style plenty of times, but penny loafers are now officially classics. This means every brand has a model.

Not only will searching for penny loafers leave you overwhelmed, but about half of what’s out there isn’t great. Stick to the five best pairs rounded up here.

Best Overall
  • Sleek taper, smooth saddle, and almond toe provide a refined aesthetic that can also be worn casually
  • Beautifully waxed full-grain leather construction boasts a high level of hand craftsmanship
  • Combination of steel shank, heel cap, and shape-forming footbed affords both sturdiness and comfort
Best Suede
  • Made with repello leather, calfskin suede processed for extra water resistance and richness
  • Goodyear welted construction ensures resoleability and impressive value for price
  • Snug collar gives secure but not overly tight fit
Best Budget
  • Slimmed down take on the American penny loafer looks modern and classy
  • Comfortable right out of the box
  • Sophisticated stacked heel and solid outsole make the shoe look way more expensive than it is
Best Luxury
  • Shell cordovan is crease-proof, exceptionally shiny, and lastingly durable
  • Wide range of sizes, widths, and outsole variants offer a high level of customization
  • Custom cork insole will perfectly accommodate your exact foot shape
Honorable Mention
  • Traditional American penny loafer design, with smaller “beefrolls” for more versatility
  • Three outsole options including a thick-lugged winter-friendly version
  • Calfskin leather has high strength-to-weight ratio, for softness and durablity

When it comes to style, I’ve been told that you can’t be both particular and universal at the same time.

Here’s what this means.

You can either wear something distinct and be the flavor of the week, or just go full boring so you never have to look back at old pictures in embarrassment.

I don’t believe this is true. Sure, it’s a tough balance, but the humble penny loafer is a foolproof example of this being achievable.

When you’re wearing good penny loafers, compliments will definitely pour in. But, they’ll never go out of style either—which is the case with the five best penny loafers rounded up here.

How Did I Come Up With My List?

As far as immediate research goes, I tried on, read about, and consulted experts on upwards of 20 pairs in the past few weeks. 

I will say though, as someone who’s had a uniform of some type since five years of age, penny loafers were always the go-to casual shoes put upon me. My school uniform allowed us to wear loafers on Fridays, as does my traditionally suit-and-tie day job attire today. And I’ve been in my industry for over a decade.

Along with Oxfords, I’ve worn hundreds of penny loafers. I’m an accidental expert, and I remember all of the pairs that were terrible and all of the pairs that did their service right.

Since not all feet and lifestyles are made alike though, I also spoke to colleagues, friends, and clients regarding their experiences with different models.

5 Best Men’s Penny Loafers Right Now

Best Overall: Beckett Simonon Cohen Loafer

The design approach taken on the Cohen Loafers is classic Beckett Simonon. 

They combine best practices from tried-and-true templates to build shoes that can sit comfortably in most dress codes. Arguably, the black versions can be worn in any situation, since their tonal outsole lets you pair them with a tuxedo. 

The silhouette tapers elegantly and the saddle lacks beefrolls, like European-style loafers. However, the almond-shaped toe gives its more brawn, like an American penny loafer, while still maintaining the overall moderate look.

Can you wear these with jeans? Yes. To a board meeting with your boss? Go for it.

And of course, as Beckett Simonon (a shoe company founded by leather experts) does, they utilize this very expertise and their industry connections to source real artisans and premium materials. 

The Cohens are handcrafted and hand-finished using supple full-grain leather and a combination of shea butter and wax to ensure even the darkest colorways are vivid and not murky.

Moreover, these guys are super comfortable. The insoles accommodate the contours of your feet, while the Vachetta lining naturally fights odors and uncomfortable temperatures. Even the added rubber heels make walking or standing for long periods of time pretty easy-going.

What I Like

  • With its almond-shaped toe and smooth no-beefroll saddle, this shoe is a middle-ground between a sleek Italian loafer and a brawnier, more casual American one, making it especially easy to pair with a range of outfits.
  • Its handcrafted construction and full-grain leather body makes it equal to models several price points above its sub-$300 category.
  • The steel shank provides sturdiness, while the Vachetta interior, rubber heel cap, and Blake-stitched construction balance it out with comfort, offering easy wear as well as support.

What I Don’t Like

  • With Beckett Simonon, I always say you’ll pay more with time than money. The made-to-order model sometimes means a long waiting and shipping time.

What Do Other Reviewers Say?

It’s hard to find good penny loafers at non-luxury prices, which is why reviewers of the Cohens praise Beckett Simonon for all of their middle-man cutting, made-to-order business practices.

Style and construction aside, the Cohens also get a lot of love for their functionality.

Many report they’re immediately comfortable, while others mention a quick break-in period. Moreover, the almond-shaped toe not only gives these shoes that signature Beckett Simonon visual versatility, but it provides a lot of volume and breathing room, even for wide-footed folks.

The Verdict

The Beckett Simonon Cohens are an easy purchase, thanks to their looks, their build, and their functionality.

You’re essentially getting a $400 pair of shoes, handcrafted and hand-finished using full-grain Italian leather, for about half their price. Second, features like the steel shank and the rubber heel cap guarantee that you don’t have to choose between strength and comfort.

And finally, the well-balanced design allows you to wear these as everyday shoes or formal ones. They also get extra credit from me because of their four, nuanced shades of brown.

Best Overall
Beckett Simonon Cohen Loafer

With their smooth saddle and slight taper, the Beckett Simonon Cohen Loafers are elegant and unstuffy. You can wear them with anything, and their handcrafted full-grain leather construction offers unique value.

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Best Suede: Grant Stone Traveler

I remember the first time I pulled the Grant Stone Travelers out of their box.

I immediately noticed some off-template details, like the flat lip and the saddle that descends past the collar on both sides of each shoe. Of course, I also noticed the buttery suede and the classy-looking stacked heel.

It wasn’t until I got them on my feet that I realized how much I loved them, and still love them. With this overall clean and subtle look, the Travelers are easily one of my most versatile shoes. The flat silhouette matches the most casual, non-sweat-pant combinations, while the lack of complexity and obviously premium suede goes well with any suit.

They even look smart with shorts, so, as their name suggests, the Travelers are perfect airport shoes for any kind of trip, from vacation to business.

Grant Stone is an interesting brand because their shoes are made in China, but the founders have real relationships with their partners there. It’s not just cheap, shortcut-focused outsourcing. Because of this, the Travelers are both Goodyear-welted and made with a special calfskin called Repello, which is processed for better water resistance and richness.

One of the founders, Randy Gilmore, has worked for decades in the Chinese shoe industry and, with hands-on experience and meticulous research, chose the Xian factory that Grant Stone works specifically with.

What I Like

  • The suede is strong yet soft, with a velvety, napped surface and rich color.
  • Its Goodyear welted construction makes this shoe exceptionally durable and resoleable, and also wildly impressive at this price point considering how good the suede already is.
  • With its flat silhouette and straight-forward design, this shoe can be worn in any non-athletic context.

What I Don’t Like

  • I love how the fitted collar keeps the back of my foot in place, but it can be difficult to put on when you’re wearing it with midweight socks. .

What Do Other Reviewers Say?

Reviewers love how sturdily-built the Travelers are, especially for their price. I’ve even seen some reviewers break them in by putting a high-pressure hose to them.

Grant Stone also gets a lot of praise for their packaging, which I agree with. Each shoe is individually placed in branded dust bags, both of which feature a drawstring with elegant wood beads. It ensures the shoes stay put and secure during shipping, while also providing a fun unboxing experience.

Some reviewers complain about the shoe being too loose. Clearly, they didn’t read the description on the website that instructs you to size down half a size from your regular Brannock.

The Verdict

Uniquely, the Grant Stone Traveler Penny Loafers are way more affordable than equally well-built loafers, yet offer incomparably better quality than any made-in-China fashion shoes. Basically, they’re just honestly-priced, honestly-built premium pieces of footwear.

They’re Goodyear-welted with high-end suede, flaunting a simple yet adaptable look that can be worn basically anywhere. They’re definitely my go-to shoes when I can only take one pair with me on a lean-packed trip.

Best Suede
Grant Stone Traveler

At their price, the Grant Stone Travelers pleasantly surprise with hearty Goodyear-welting and topnotch suede. Their honest, no-nonsense design makes them as adaptable as they’re functional.

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Best Budget: Banana Republic Factory Leather Penny Loafer

The Banana Republic Factory Leather Penny Loafers are a simplified, modern take on the robust American penny loafer. And by that I mean that they take all of the features that make that template so muscular (and therefore more casual), and simply allude to them.

Instead of two giant beefrolls at the side of each saddle, there’s simply stitching where the top meets the sides. And while the toe area is slightly rectangular in its shape, there are swerves instead of hard edges.

These have that tried-and-true vibe, but are visually well into the 21st century.

The leather itself is mid-tier, but not bad, though it looks great in black and is well waxed. At first glance, or even second or third, you’d think it was a higher grade leather than it actually is.

And finally, these shoes are comfortable at every angle they could be. The footbed is soft right out of the box, and the edge of the lip doesn’t stab you the way the edges of unfinished leather often does. This is rare for budget shoes. They’re also more flexible than hard, unbroken-in leather from premium shoes.

What I Like

  • The slimmed-down overall shape and smooth-edges is a less beefy take on the classic American penny loafer, making this shoe subtly modern and unique.
  • This shoe is immediately comfortable, fits true to size, and requires no break in period at all.
  • The finishing and slightly rounded edge of the lip sits flexibly on your front ankle, unlike the stabby edges of poorly-finished budget shoes found at this exact price point. .

What I Don’t Like

  • Though this mid-tier leather looks great in black, there is in fact just one colorway.

What Do Other Reviewers Say?

Despite how I point out that the leather isn’t the best, all of the five-star reviews point out how much they like the leather quality. I agree in the sense that, as mentioned, it looks pretty good for its price and no one is going to get their face or hands anywhere near your shoes in everyday situations.

There’s one complaint about how the toe isn’t exactly round, and isn’t exactly rectangular, and is, “a weird shape for a penny loafer.” Funnily enough, it’s one of the reasons I like these shoes, so to each his own.

The Verdict

If you’re looking for a handsome, comfortable, and classic American penny loafer for way under $200, then go for Banana Republic’s Factory Leather Penny Loafer.

You can wear it right out of the box, and the burnished black leather looks sophisticated next to the stacked dark brown outsole.

Best Budget
Banana Republic Factory Leather Penny Loafer

Comfortable right out of the box, the Banana Republic Factory Penny Loafers are as easy to wear as they are to style. The slimmed-down take on the American penny loafer and the handsome heel stacking also make these budget shoes look more premium.

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Best Luxury: Allen Edmonds Shell Cordovan Randolph

As simple as a traditional penny loafer is, Allen Edmonds somehow manages to pull out all the stops successfully with the Randolphs.

True investment shoes, these loafers are made out of shell cordovan, which is equine leather taken from the highly fibrous part of the rump. The resulting material is astonishingly crease resistant, one of the strongest types of leather in the industry, and so bright that even the darkest shade of shell cordovan offers beautiful lightplay. 

Allen Edmonds’ 79 last is used, which features a tapered back, for a low fit that brings about a resort-like class when you wear them without socks, or a professional and stately aesthetic when you wear them with tonal socks.

And since Allen Edmonds is one of few American heritage brands that didn’t cave in to cost-focused practices, the Randolphs flaunt a handcrafted quality and a 360-degree bench welted construction.

This means that the leather footbed, cork insoles, and the heel are fully secured to each other, a solid stability that you can feel when you walk around in these shoes.

What I Like

  • This shoe is made out of shell cordovan, which is one of the finest leathers on the market thanks to its resistance to creases, its exceptional shine, and its lasting durability.
  • The Randolph comes in a wide range of sizes, widths, and outsole variants.
  • With its custom cork insole and 360-degree bench-welting, this shoe is comprehensively built for both comfort and strength.

What I Don’t Like

  • All of Allen Edmonds Goodyear-welted leather shoes have a pretty substantial break-in period, but this is especially so with their shell cordovan shoes. .

What Do Other Reviewers Say?

While several reviewers admitted initial hesitance because of the high price of these shoes, virtually all of them also concede that they’re completely worth it. After that grueling break-in period, the Randolphs become as strong as they are lush, and fully conform to your feet.

A lot of men with especially small feet praise Allen Edmonds for going as small as a men’s 5, while those with especially large feet do the same for the fact these shoes come in a 16.

The Verdict

The Allen Edmonds Shell Cordovan Randolphs are definitely forever shoes. The non-creasing and extra strong leather maintains its flawless look, as well as the overall integrity of the shoe. This is further cinched by the all-around Goodyear welt construction.

Even more, you can customize these shoes on several levels, meaning they’ll be uniquely yours once you’ve broken them in.

Best Luxury
Allen Edmonds Shell Cordovan Randolph

The Allen Edmonds Randolphs are made out of lustrous, crease-resistant, and durable shell cordovan. They’re also bench-welted all around, providing stability and durability for a long-lasting, high-quality piece of footwear.

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Honorable Mention: Velasca Maester

If you like the idea of modernized American penny loafer, but want something a little further up in tier than our budget pick, allow me to introduce you to the Maesters from Velasca.

Between the beefroll-like stitching on the saddle edges and the raised area where the top meets the sides, there’s a lot of topography on these shoes without looking overly muscular. That is, unless you go for the winter Vibram lugged sole.

Which brings me to a cool aspect of these shoes on the function front. You can get them in different outsole variations at no extra cost. You can go for a dressy leather outsole or a grippy rubber one, or a deeply-lugged winter outsole.

And finally, these shoes are made with calfskin leather, which thanks to its extra tight grain, is strong yet soft, and much smoother than regular bovine leather.

What I Like

  • The design is that of an on-template American penny loafer, but smoothed out allowing you to wear this shoe on dressier occasions as well.
  • At no extra cost, you can choose between a leather outsole, a rubber outsole, or a lugged rubber outsole for extra grip.
  • The calfskin leather is lithe and tough, while also displaying an extra smooth surface that takes to oils and light exquisitely.

What I Don’t Like

  • This is subjective, but after reading the reviews, I know at least half of the people out there agree with me. The lip has a frayed-edge design, which though subtle, is a bit too funky for me.

What Do Other Reviewers Say?

Reviewers love the American heritage look of these shoes, and how the different outsole variations allow you to accommodate different lifestyles.

As mentioned, people are split on the lip design.

Velasca also gets a lot of love for their customer service. They offer really quick shipping, promising delivery no more than five days from your order. Plus, if you live in the US or Canada, shipping is free for anything above $100.

The Verdict

The Velasca Maestros are a fashionable take on the American penny loafer, without compromising its Americana aesthetic. It’s the perfect upgrade for those of you who can’t let go of your grandpa-esque penny loafers, but want to look more of-the-day. It’s the difference between an oversized musty, fraying cardigan, and a classic, but well-fitted, clean-lined cashmere one.

Moreover, the construction is excellent, from the calfskin leather to the different outsole options.

Honorable Mention
Velasca Maester

The Velasca Maester showcases a traditional Americana look, that can be worn casually, formally, indoors, and outdoors. They’re made from soft but strong calfskin, and come in three outsole variations, including one with extra thick lugs.

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3 Amazing Ways to Style Penny Loafers

We all know that penny loafers go perfectly with a full suit, as well as a t-shirt and jeans. Did you know that you can wear them with everything in between too? 

Check out these stylish gents to see what I mean.

1. Vacation Suiting

I love how this outfit has the two basic components of a suit: The jacket and the trousers. 

However, with the patterned blazer, wide collar cotton polo, and cream pants (brilliantly tonal with his hat), he took the fact that penny loafers go perfectly with a suit, and used that as a jumping off point to create a casual yet classy broken look. If you’re less fashion forward than him, you can always ditch the hat and scarf, and go for a non-patterned jacket.

2. Workwear Adjacent

Since penny loafers are so topographical, you can pair them with garments that are equally as sculptural. This jean jacket is a great example, though I appreciate the high-low combination of adding a tie in there — by the way, penny loafers are the perfect shoe for high-low combos.

This outfit would also work with a utility jacket or fitted work pants.

3. Weekend Elegance

Here’s a fun fact: 99% of the time, you can replace any well-styled outfit that includes sandals or low-profile white sneakers, with penny loafers. This elegant combination is a perfect example. In fact, even if you swamped his white pants for shorts, the loafers would still work,

Understated Yet Distinguished

Thanks to their timeless styling and bang-for-buck materials and construction, the Beckett Simonon Cohen Loafers win the award for best overall. However, you can save several hundred dollars with the Banana Republic Penny Loafers, which though not top-tier, are perfectly worth their price and are comfortable right out of the box.

Beckett Simonon Cohen Loafer

With their smooth saddle and slight taper, the Beckett Simonon Cohen Loafers are elegant and unstuffy. You can wear them with anything, and their handcrafted full-grain leather construction offers unique value.

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Far on the other side of the spectrum are the Allen Edmonds Randolphs, made of luxurious Shell Cordovan. 

Prefer suede? The Grant Stone Travelers are actually Goodyear-welted. Love an Americana style? The Velascas are your guy.

Grant Stone Traveler

At their price, the Grant Stone Travelers pleasantly surprise with hearty Goodyear-welting and topnotch suede. Their honest, no-nonsense design makes them as adaptable as they’re functional.

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Truly, there’s a penny loafer model out there for every personal style.


Do men still wear penny loafers?

Yes. The Penny loafer is a classic smart casual shoe, and depending on its design can even be worn formally.

What are the most comfortable loafers for men?

Any loafer with a cork midsole that conforms to your foot will eventually be custom-level comfortable for anyone without specific foot conditions.

Why do men put pennies in their loafers?

Back when pennies could get you a call on a payphone, men used the saddle on a penny loafer as a storage space. These days, the saddle is simply decor.

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