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25 Updated Penny Loafers and Other Loafers in 2021

25 Updated Penny Loafers and Other Loafers in 2021

Menswear in 2021 is all about hybrid style, and loafers serve as the paradigm of this. We expect drawstring waists on our chinos, flap pockets on our joggers, sneakers to double as dress shoes, and, in the loafer’s case, slippers that can handle the outdoors.

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Many of us are heading back to the office – or might already be there, commuting in for the nine-to-five. We’ve been hearing how dressing up will make a strong return, but much of that appreciation is gradual. No, we’re not heading out everywhere in athleisure, but the suits we should all be wearing seem looser and more comfortable, T-shirts are replacing dress shirts, and men’s loafers have created a perfectly acceptable (and more accessible) alternative to traditional oxfords, derbies, and brogues.

loafers for men

Why Men’s Loafers and Why Now?

There’s a reason for this – and its not just firmly holding onto the comfort we’ve all gotten used to over the past year. Loafers, at least where menswear is concerned, exemplify versatility. They prove their worth with your business casual and smart-casual wardrobes, aren’t a stranger to cocktail dress codes, and have an ease, almost like Vans slip-ons but elevated, with jeans and chinos. While we’ve thought of loafers primarily as an ‘80s prep staple, newer materials and patterns divert them away from this impression, and men are now discovering why they’re one of the most adaptable shoes you can own.

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If you want to stay traditional, men’s loafers are constructed out of leather or suede – velvet, in select cases, but never cotton or another textile fabric. At that point, you’re fully immersed in the world of slip-ons. Suede requires an inordinate amount of care, thus making leather the predominate material.

Style wise, loafers started out practical, worn by fishermen in Norway, before they, like chinos and polo shirts, were adopted by Ivy League college students in the 20th century, likely for their ease. Over nearly the past century, they’ve been a cornerstone of preppy style, but current reworkings of these conventions have partially shed such assumptions.

man standing wearing loafers

If you’re looking to explore loafers – espadrilles and boat shoes don’t count, even though they’re frequently grouped in – here’s where you can go started.

Classic Loafers

While several styles of loafers exist, the classic trifecta includes the Weejun, the penny loafer, and the tassel loafer.

G.H. Bass & Co. pioneered Weejuns – a reference to the shoe’s Norwegian origins. Penny loafers grew out of this, named after the habit of placing a penny in the front slot. Tassel loafers, meanwhile, are just as they sound. A tassel adorns the front, apparently adapted from a pair of oxfords, for a showier appearance.

Difference Between Tassel Loafer and Penny Loafer

To begin let’s start with the question: Why are they called penny loafers? The penny loafers meaning dates back almost 100 years. When the shoes first became popular in the early 1900s, people still needed pennies to use public telephones. They would store their pennies for the phone in the handy slot on the loafer’s strap, giving the shoe its name: “penny loafer.”

As you might have guessed, the primary difference between a tassel loafer and a penny loafer is that the latter does not have a tassel design. Simple penny loafers are a fantastic companion for slacks, corduroy pants, and even chinos. On the other hand, men usually wear tassel loafers for more sophisticated events.  

Where to Wear Them

Every man who has a loafer can rock it at any event if they know how to style it well. 

We love pairing loafers with smart casual outfits, semi-formal events, and even our stylish casual clothes. Many men also ask: Do you wear penny loafers with socks? The answer depends on your personal style. We love the no-sock look, but you can opt for an invisible sock to give you a sleek look while protecting your feet.

penny loafers

How to Style Your Outfit with a Pair 

Casual loafers are amazing with khakis, denim, and even shorts when worn sockless during the summer. We recommend wearing loafers with a blazer or two-piece and three-piece suits for weddings and other events where a little class is needed. 

Our Shortlist

Tassel Loafers

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Polo Ralph Lauren Booth Calfskin Loafers

These loafers aren’t just classic in appearance: They reflect bygone attention to craftmanship through handmade Goodyear welt construction and refined materials like soft full-grain leather and a cork insole.


STACY ADAMS Men's Tazewell Tassel Slip-on Loafer

Stacy Adams Tazewell Tassel Slip-on Loafer*

For the ultimate refined-looking loafer, it’s hard to say no to the Stacy Adams men’s Tazewell Tassel Slip-on Loafer. It has four color selections and comes with microfiber material with a suede tassel. This loafer is lightweight and features memory foam for superior comfort. We can last all day long without feeling like our feet will fall off in this shoe. 


STACY ADAMS Men's Bianchi Tassel Slip-on Loafer

Stacy Adams Bianchi Tassel Slip-On Loafer*

Stylish is the best way to describe this pair of loafers. It’s the best loafer to get if you’re looking for a chic version of the staple shoe. Since this loafer has 100% leather with wales print and tassel design, it can withstand wear and tear. Plus, it sports a unique silhouette to accentuate your whole look. 


Driver Club USA Men's Made in Brazil Hampton Leather Sole Tassle Loafer

Driver Club USA Hampton Leather Sole Tassel Loafer*

With suede and leather variants, it’s hard not to talk about this tassel loafer. Skilled artisans from Brazil beautifully handcraft these penny loafers with tassels, giving them a rich yet buttery-soft feel. Whether you want to wear it for work or leisure, you’ll enjoy its arch support, flexible sole, and footbed. 


Penny Loafers

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Hugo Boss Leather-Lined Penny Loafers in Polished Leather

You’ll forget about school-uniform penny loafers with this polished, smooth, and nearly seamless pair that’s dressed up for business meetings and nights out.


Lexington Tassel Weejun Loafers

G.H. Bass & Co. Men’s Lexington Tassel Weejun Loafers*

How many ways can you rework an original? These Weejuns don’t stray too far from their template, here adding tassels to hand-stitched leather construction with a stacked heel.


Cole Haan Men's Hyannis Penny Loafer II

Cole Haan Hyannis Penny Loafer II*

As an excellent addition to a preppy wardrobe, you can wear these Cole Haan Men’s Hyannis Penny Loafers with checkered shirts and chinos. The style and material make it the perfect accompaniment to any casual weekend look. Its rubber sole also looks good when paired with jeans.


Cole Haan Men's Wagner Grand Penny Loafer

Cole Haan Wagner Grand Penny Loafer*

You can never go wrong with this Cole Haan loafer. This shoe will be any person’s go-to for semi-formal events and even date nights. It looks sleek and luxurious and will help make a good impression. It also has tremendous value for the price, so you can trust this shoe is a smart purchase.

Rockport Men's Classic Penny Loafer

Rockport Classic Penny Loafer*

This list wouldn’t be complete without a classic brown pair option. As one of the best penny loafers for men, it is made with 100% leather and comes with a 1-inch heel for a more refined look. Its material is also simple to clean. 


Cole Haan Men's Loafer

Cole Haan Loafer*

Don’t be fooled by its appearance, as loafers can be casual, too. While you might not want to wear these Cole Haan loafers with sweatpants, they are a perfect casual pair. The premium leather goes well with broken-in chino pants, jeans, and even a good beanie


Bostonian Men's Birkett Way Penny Loafer

Bostonian Birkett Way Penny Loafer*

As the perfect combination of modern and retro style, you can pair this Bostonian Men’s Birkett Way Penny Loafer with cardigans, rugged tees, and jeans. It is the epitome of simple and sophisticated design. 


Horsebit Loafers

Many will argue that a horsebit loafer falls within the classic spectrum. Yet, in terms of appeal, they cross over from unassuming slip-on dress shoe into a statement maker, thanks to the hardware adorning the top.

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Gucci Men’s Loafer with Interlocking G Horsebit

Horsebit details are pulled from Gucci’s archives, bridging the brand’s lengthy past as a leading leather goods manufacturer with the androgyny-driven Harry Styles-modeling era.


Loafers_-_Lacoste_Men_s_Ansted_Driving_Style_Loafer

Lacoste Men’s Ansted Driving Style Loafer*

Contrasting lugs matching a stripe of fabric underneath the hardware play up the go-anywhere angle while adding a touch of statement appeal.


STACY ADAMS Men's Neville Moc-Toe Slip-on Penny Loafer

Stacy Adams Neville Moc-Toe Penny Loafer*

This Stacy Adams pick is another one of our best penny loafers. It is made with suede and lined with leather. This shoe is very comfortable thanks to its fully cushioned insole packed with memory foam for shock absorption. Plus, it has a great classic color that will match any outfit. 


Driving Loafer

Some call this a driving shoe, but the intent is all the same. A moccasin-meets-loafer silhouette lets you move outdoors with a gripper outsole. You might not wear these to go hiking, but they’ll do you well once your journeys take you away from the city sidewalks.

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Polo Ralph Lauren Roberts Leather Driver Loafers*

The vibe of a boat shoe receives an upscale take. Here, burnished leather upgrades the summer-in-New-England staple, while rawhide laces and a moccasin-style front offer a clear allusion.


Loafers_-_Kenneth_Cole_REACTION_Men_s_Darton_Slip_On_Driving_Loafer

Kenneth Cole REACTION Men’s Darton Slip-On Driving Loafers*

Get the grip you seek and bold style you want from these suede-like loafers in less-typical colorways, complete with a moc toe and rawhide laces.


Venetian Loafers

Venetian loafers embody minimalism, nearly seamless with a one-piece design excluding where the shoe meets the outsole. Beyond this silhouette, the adornments you’ll notice on other styles listed here are gone – no tassels or hardware to be found. Instead, the fabric, often suede or velvet but more recently patterned, becomes the focus.

Loafers_-_Hugo_Boss_Suede_loafers_with_embossed_logo

Hugo Boss Suede Loafers with Embossed Logo

We tend to think of Venetian loafers as more formal in character. This pair defies expectations with a rubber outsole contrasting against the smooth, one-piece suede body.


Loafers_-_Frye_Men_s_Chris_Venetian_Loafer_Flat

Frye Men’s Chris Venetian Loafers*

Keep it simple yet sophisticated. These Frye Venetian loafers do that through a one-piece design with a matte finish, variety of unexpected hues, and a low, almost flat heel that adds to its overall effortless quality.


Chunky-Soled Loafers

Blame the dad shoe trend from a few years ago. These days, you’ll come across all types of shoes with a thicker, more lugged outsole, and loafers are no exception. Consider this the platform loafer of the late 1990s adapted for men.

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Fendi Brown Leather Loafers

While these aren’t quite to platform heights, the chunkier, lugged outsole and exaggerated boat shoe-inspired body add an almost campy take on the traditional loafer.


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Dr. Martens Adrian Smooth Leather Tassel Loafers

This platform shoe brings the durability men and women have loved about Dr. Martens boots for decades and pairs it with a chunkier tassel loafer silhouette.


Statement Loafers

The sky is the limit – maybe even literally, considering the preponderance of cloud prints over the past year. Two-tone, velvet, and patterned designs have established their corner of the market, adding everyday appeal to what might come off as a luxury slipper.

Loafers_-_Purple_Label_Chalmers_Crocodile_Loafer

Ralph Lauren Purple Label Chalmers Crocodile Loafer

Embossing highlights the 100% crocodile exterior, giving this classic silhouette a luxurious, if not somewhat adventurous, upgrade.


Loafers_-_Stacy_Adams_SWAGGER

Stacy Adams Men’s Swagger Studded Ornament Slip-On Driving-Style Loafer*

Absolutely nothing’s subtle about this shoe, starting with the smoker-style Venetian silhouette to the all-over studs and, finally, the badge-like branded medallion on the vamp.


Loafers_-_GH_Bass_LARSON_SUPER_LUG_WEEJUNS

G.H. Bass & Co. Larson Super Lug Weejuns

Just because it’s classic, that doesn’t mean it’s boring. G.H. Bass gets with the times, adapting its Weejuns to the more fashion-minded consumer with a two-toned colorway and chunkier outsole.


ELANROMAN Men's Loafers Tassels Penny Slip-On Luxury Wedding Shoes

Elanroman Loafers*

If you’re looking for a stylish loafer that is super comfortable but won’t break the bank, this shoe is for you. The Elanroman Men’s Loafers is a unique modernized shoe that adds an element of fun to any formal outfit. It is lined with silk and leather, making it look luxurious enough to wear at weddings and holiday parties.


Men's Vintage Velvet Embroidery Noble Loafer Shoes Slip-on Loafer Smoking Slipper Tassel Loafer

Vintage Velvet Embroidery Loafer*

This vintage shoe is the ultimate loafer for those who do not shy away from making a statement. This two-toned loafer is anything but boring. It has a quality metallic upper and blocked heel, making it a fantastic addition to flashy suits to wear for parties or prom.


Every Man Needs a Trusted Pair of Loafers 

Wearing loafers is an awesome way to shake up any fashion routine. Whether men are in the mood to dress up or be casual, these best penny loafers and tassel loafers for men will look great with just about anything. 

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