casual penny loafers mens

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We’ve said it before, we’ll say it again: the single most valuable thing in menswear is versatility. Which is enough reason for us to justify why you need a pair of loafers in your wardrobe this season.

These instantly recognisable shoes are as versatile as footwear comes; slip-ons that slip into a wide range of dress codes with ease. They work with suits, cropped trousers, pinrolled jeans and even shorts if they’re the right kind (slim-cut, finishing just above the knee, thank you very much).

Going for a preppy Americana look? You’ll need some loafers. Mediterranean louche? Loafers. Tailoring? Even then, loafers can finish off a Savile Row look with a cool, modern edge.

“A good penny loafer or, if you are feeling fancy, tassel loafer, looks just as good with a casual unlined suit or sharp pair of trousers and Oxford shirt,” says Mr Porter shoe buyer David Morris. “But during the warmer months, don’t be scared to wear them with shorts and a short-sleeved camp collar shirt.”

Loafers are usually made from either suede or leather, so most pairs will need a little wearing in. “Width can also play a huge part in the overall fit,” says Morris, “and those with a high instep may need to go a size up.”

mens casual loafers with jeans

Casual Penny Loafers Mens

Lincoln | Natural in 2020 | Loafers men outfit, Loafers men, Mens casual  outfits

The Different Styles Of Loafers

Loafers have a long and storied heritage in menswear, and all the main styles have their own history.

First, there’s the classic penny loafer. Despite being a symbol of Ivy League fashion, it actually originated in Norway before later being reinvented by American firm G.H. Bass & Co. The style gets its name from the sit on the front of each shoe, which doubles up as a place to store a penny.

Then there’s the tassel loafer. The story goes that this silhouette was born in the 1950s, when Oscar-winning actor Paul Lukas asked American shoemakers Alden to recreate a pair of Oxfords he found in Europe that had little tassels at the ends of the laces. The result was an instant classic, and many competitors went on to release their own versions of this much-loved style soon after.

There’s no doubt that the horsebit loafer is the go-to dress shoe within the realm of loafers. As its name suggests, the horsebit takes its influence from equestrian style – and we have Gucci to thank for its existence.

And don’t forget the slipper. This style of loafer is characterised by its leather sole, slight heel and velvet or suede uppers. It works just as well as an alternative to the more traditional dress shoe as it does for smartening up a casual outfit.

When you’re ready to add a pair to your collection (now, man, now), these are the brands to slide into.


Gucci is a turn-to choice when you want to show off, but if we’re talking about loafers, it’s not just about stunting. The Italian label played an integral part in the enduring loafer styles we still wear today.

Gucci continues to refine the traditional silhouette even today, with styles like the fringed leather loafer, inspired by the punk movement of the 1970s and 1980s, and its distinctive horsebit design with an embroidered bee symbol.

Granted, they’re not the cheapest on the market, but for the extra investment, you can expect luxury touches like a lamb fur or quilted satin lining.

Black Jordaan horsebit-detailed leather loafers | Gucci | NET-A-PORTER

Brooks Brothers

Brooks Brothers is America’s oldest clothing retailer, with a heritage dating back almost 200 years. The brand offers a discerning range of traditional loafers, and the quality is almost second to none.

Sitting at the slightly more accessible end of the luxury market, Brooks Brothers’ penny and tassel designs are crafted from premium materials like supple cordovan leather, pure French calfskin and kudu antelope suede. All of this makes Brooks an excellent choice if looking for a loafer to finish a suit.

Leather Penny Loafers - Brooks Brothers

G.H. Bass & Co.

This American heritage company goes back to the 19th century and balances its traditional roots with modern tastes. G.H. Bass is worth a browse if you’re looking for something preppy with the history to back it up.

Look out for the classic Weejun loafers, a silhouette that can be traced to the brand’s early years. You can find it in traditional colours and finishes, but you’ll also see it styled with more modern finishes.

Shop brown G.H. Bass & Co. weejuns larkin tassel loafers with Express  Delivery - Farfetch


Reiss has well and truly cornered the premium end of the British high street, and its choice of loafers match its wider smart-contemporary vibe.

The retailer stays true to tradition while injecting seasonal touches, and its collection offers an array of more casual options for when you want to dress down.

Keep an eye out for butter smooth suede styles that pair excellently with cropped trousers. It’s a summer uniform for smarter dress codes.

Reiss Farah Leather Tassel Loafers, Black at John Lewis & Partners

Charles Tyrwhitt

A traditional British brand brimming with charm and elegance, Charles Tyrwhitt’s loafers are, as you’d expect from a Jermyn Street powerhouse, built to last.

The retailer’s collection consists of both leather and suede loafers in a refined choice of brown and black shades that are perfect additions to your work-week wardrobe.

If tassel loafers are your thing – this brand is particularly gifted on this front. These debonair styles are ideal for the man who appreciates good quality, craftsmanship and a little extra attention.

Tan Yardley Suede Apron Tassel Loafers Size 9 R by Charles Tyrwhitt: Clothing

John Lobb

One of Northampton’s finest, John Lobb offers a handsome collection of loafers, with shoemaking expertise that stretches back almost 170 years. As such, expect finer touches such as hand-stitching, lightweight finishes and expertly cut leather.

The collection is rooted in traditional styles from the 1950s, but styles are refined with a contemporary edge, fitting for any modern man’s wardrobe. Prices range from £900 to £1,200 – with the odd £7,000-odd anomaly for when you’re feeling extra spendy.

John Lobb Brown Lopez Loafers | The Rake


For the man who can’t make decisions, Canadian retailer Aldo offers a wide range of loafers at reasonable prices, meaning you can afford to get a few pairs.

With some Italian influence thrown in, effortless suede numbers sit alongside standout brights and classic staples, so your every possible need is catered for at a high street budget.

Aldo Loafers For Men's at Rs 799/piece | Men Loafer Shoes | ID: 20580219888

Joseph Cheaney and Sons

Another brand from the home of British shoemaking, Northamptonshire-based Cheaney and Sons is where to go if you’re in the market for some serious, go-the-distance loafers.

The award-winning, heritage firm offers a polished range of hand-crafted loafers that are made in England – and have been since 1886.

It’s the quality that puts Cheaney’s loafers head and foot above the competition. For our money, its penny loafers are near-perfect expressions of the style.

?Joseph Cheaney & Son Loafer | Dress shoes men, Loafers men, Stylish shoes

Marks & Spencer

Marks and Spencer’s is the old high street failsafe that never lets us down, especially when it comes to menswear staples that have been around for generations.

While the chain’s loafers are all as reasonably priced as you’d expect, bear in mind that most are also more on the casual side, with a wide offering of dressed-down suede options in particular.

Patent Tassel Loafers | M&S Collection | M&S


Founded in 1884 by Charles H Alden, the eponymous firm is rumoured to be the inventor of the tassel loafer. Today, the New England shoemaker can be found in concessions around the world, although it stays close to its traditional preppy roots.

Each style is cut from the best quality leather, including a full leather lining, and is built for comfort and longevity. Check out its range for fellow all-American staple J. Crew for a more contemporary take on the classic loafer.


Dr. Martens

To give this traditional dressed-up style of shoe a bit of attitude, try a brand with some form when it comes to stylish sub-cultures.

Dr Martens’ take on loafers is as chunky as they come, but don’t go thinking that the dedication to quality is any less than a Northampton stalwart.

As well as that famed mirror-like finish, you get Goodyear welting – a guarantee of hard-wearing construction – as well as the all important air-cushioned sole.

Dr. Martens Adrian Loafers Black Smooth - Flats

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Best Loafers for Men to Buy

Best Loafers Overall: G.H. Bass Larson Weejuns

G.H. Bass Larson Weejuns

In 1936, G.H. Bass was the first American brand to create a local interpretation of the slip-on, Bass Weejuns, a pun off, you guessed it, “Norwegian.” It’s also referred to as the original penny loafer, because legend has it, students would tuck a one cent coin in the front slot of their shoes to use for pay phones. Almost a century later, these loafers are still G.H. Bass’ bestsellers, and can be worn in retro or modern style. Pair them with rugged jeans and a gray tee for a dash of devil-may-care attitude, or team them up with a khaki chino suit. To us, those sound like the best loafers overall … period. 


Best Luxury Loafers: Gucci Leather Bit Loafers

Gucci Leather Bit Loafers

These instantly recognizable leather bit loafers have become a status symbol among investment bankers (and have inspired a legion of knockoffs), but they look just as polished outside of Wall Street. Made to be worn with your sharpest suit, or your simple shirt-and-jeans combo, these Gucci loafers can instantly elevate any fit for generations to come, and they’ll live up to your investment.


Best Statement Loafers: Artemis Design Co. Sumak Kilim Loafers

Artemis Co loafers

Artemis Design Co., an Istanbul-based footwear upstart, has rightfully gained a cult following for their intricately designed, head-turning shoes. Case in point: these gorgeous loafers sourced from Turkish carpets, and embroidered with red, white, and blue prints of animal iconography.


Best Leather Loafers: Allen Edmonds Lake Forest Penny Loafers

Allen Edmonds Lake Forest Penny Loafers

Ready to invest in the best leather loafers? Of course you are — that’s why we’re here. Allen Edmonds takes the same meticulous approach to these sleek black loafers as it does with its durable dress shoes and boots. This means you can wear these handcrafted leather loafers with everything from a navy cotton suit to slim black denim and a white Oxford shirt (think Alex Turner a la the Arctic Monkeys). 


Best Suede Loafers: Shoe The Bear Alonso Loafers

Shoe The Bear Alonso Loafers

If you wanted to make loafers even more versatile, opt for a suede finish, which can dress up or dress down any outfit. They should be cool and sleek, but not too precious, which is why we love these slip-ons from Shoe The Bear, which can easily be worn with summer staples like off-white jeans, a navy polo, or olive chino shorts. 


Most Comfortable Loafers: Sperry Plushwave Penny Loafers

Sperry Plushwave Penny Loafers

In general, our favorite loafers are much more comfortable than other dress shoes, but if you want an especially cozy slip-on to wear while working from home, you can’t go wrong with these Sperry Plushwave Loafers, which blend the iconic penny loafer silhouette with a well-cushioned, springy sole. Because these toe the line (pun intended) between dressy and casual, we recommend wearing them as part of a high-low combo of slim olive chinos, a white Oxford shirt, and a navy blazer. 


Best Value Loafers: Urge Marakesh  Shoes 

Urge Marakesh  Shoes 

You don’t have to spend a pretty penny to cop quality loafers. Swing through Bespoke Post to pick these breezy slip-ons, which feature hand-stitched side detailing that stylishly offers some ventilation for those hot summer days. Pair these up with linen trousers and a slub polo for laidback weekend style — just add, say, an Old Fashioned or a martini. 


Other Loafers We Love

Nisolo Alejandro Slip-Ons

Nisolo Alejandro Slip-Ons

Nisolo makes its stylish loafers ethically at one of the world’s best shoe factories, and it helps that these fashionable slip-on shoes feature a laidback silhouette and a design that’s just different enough to separate them from the pack. 


Crockett and Jones Boston Loafers

Crockett and Jones Boston Loafers

Step right into a handsome pair of loafers made by this James Bond-approved British heritage footwear maker. While Bond needs something a little more functional than loafers, these sharp brown suede loafers are perfect for us mere mortals. Wear them with white jeans and a navy polo, accessorized with classic Aviator sunglasses. 


Florsheim Berkley Moc Toe Penny Loafers

Florsheim Berkley Moc Toe Penny Loafers

We’re totally in favor of classic loafers that are a bit bold at the same time — take the eye-catching Burgundy colorway found on these Florsheim penny loafers, and at a great price, to boot. 


Yuketen Suede Penny Loafers

Yuketen Suede Penny Loafers

We’ll close things out by looking at some of the best suede loafers yet again. Yuketen makes its shoes and boots with a stunning level of craftsmanship, quality, and value, reflected in the price tag. And yet, you’ll have these loafers for years. Wear them at your cabin with olive camp pants and a white pocket tee on a breezy summer morning (coffee not required … but encouraged). 


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