penny loafers men

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Penny Loafers Men

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A country house shoe for the landed gentry, or a Norwegian farmer’s favoured style of footwear? Whatever you consider to be the true origins of the contemporary loafer, what’s indisputable is this timeless silhouette’s skilful blend of comfort and flair.

Unlike the holy footwear trinity of brogues, Derbies and Oxfords – all elegant, but a bit samey – loafers are often written off as flamboyantly ‘dandy’ or too difficult to pull off with a wide range of outfits.

In truth, these slip-on styles are anything but. Being laceless, they’re practical, and with plenty of options on offer – from traditional penny versions to luxuriously finished horsebit loafers – there’s a style for every foot. Here’s what you need to know.

Material Matters: Leather Or Suede?

Before delving into the types of shoe up for consideration, it’s worth heeding a few memos on the importance of material. Like other smart shoes, loafers are generally made using one of two fabrics: leather or suede, which both have their own strengths and weaknesses.

With their sleek and gleaming finish, leather loafers make the perfect punctuation mark for smarter looks, whether that’s a full suit or smart-casual tailored separates. Although you’ll want to be sure to keep them in good nick (taking care to clean and polish regularly), loafers made from leather are markedly sturdier than those crafted from suede and will also wear well over the years, developing a unique patina in the process.

Suede, on the other hand, should – if you have any respect at all for footwear – be exclusively reserved for the spring-summer months. Their luxurious but delicate finish means suede loafers should be protected from excessive moisture at all costs.

Suede designs also have a slightly more casual feel (though that’s not to say they can’t wear be worn with tailoring), making them a shoe-in for a warm-weather wardrobe that’s bound to be more relaxed compared than its autumn/winter equivalent.

Key Styles Of Loafer

The Penny Loafer

Irrepressibly smart, the penny loafer is the preppy footwear classic that still takes pride of place on shoe racks today, almost a century on from its invention.

Despite its connotations of US political heavyweights and film icons, penny loafers were originally conceived in Norway. Native Norwegian Nils Gregoriussen Tveranger spent his adolescence carefully studying the craft of shoemaking in America, eventually returning home to create the ‘Aurland moccasin’, a style of loafer reportedly inspired by the indigenous Iroquois.

In 1934 – prompted by Tveranger’s distinctive design – G.H. Bass & Co, a bootmaker in Wilton, Maine, released an adaptation of the Aurland. This new version, dubbed the ‘Weejun’ (sounding like Norwegian), featured a strip of leather across the front with a diamond cut-out detail – which, incidentally, doubled up as the ideal compartment for stashing a dime.

“The beauty of the penny loafer is its versatility; the shoe can be dressed up or down easily and works with most outfits,” says Gilad Yogev, former creative director of G.H. Bass & Co. Pennies will work for smarter attire like summer suiting, but they’re best used to add polish to casual or smart-casual looks. Think a varsity jacket, T-shirt and chinos, or an Oxford shirt, jumper and tailored shorts.

Men's Penny Loafers Fashion & Style Outfit Inspiration Lookbook
The best penny loafers for men

The Tassel Loafer

Although ‘tasselled loafer’ may to some ears say ‘yuppie’, the style first came about thanks, not to an white-collar dickhead, but a man by the name of Paul Lukas.

Lukas, an Oscar-winning Hungarian-born actor who starred in films including The Lady Vanishes (1938) and Watch on the Rhine (1943), was well known for his debonair style. As the story goes, at some point during the 1940s Lukas approached several shoemakers, instructing them to design a shoe that riffed on a tasselled Oxford style he’d picked up in Europe.

Low and behold, in 1950, one of America’s then-leading shoemakers, the Alden Shoe Company, released the first tasselled loafer, with initial batches flying off the shelves by 1952. A few years later, in 1957, high society outfitters Brooks Brothers started stocking their stores with an exclusive tasselled style featuring distinctive foxing (raised stitching) at the back of the shoe.

Subtly decorated in comparison to the fairly sober and traditional penny, tassel loafers satisfied mid-century America’s demand for an elegant, dressy shoe design that didn’t sacrifice practicality.

Today, arguably the best-known tassel model is the cordovan. Unlike most formal leather shoes – which are made from calfskin – cordovan loafers are crafted using the subcutaneous layer of a horse’s rump. Durable and lustrous, cordovan is also the least porous of leathers, and so highly sought after – which goes some way in explaining why you’ll need to cough up almost £550 for a pair by Brooks Brothers.

Men's Tassel Loafers Fashion & Style Outfit Inspiration Lookbook
The best tassel loafers for men

The Horsebit Loafer

With bluer blood than its brother styles, the horsebit loafer is the definitive dress loafer.

Equipped with a brass strap in the shape of a horse’s snaffle, the horsebit takes its cues from equestrian wear – not surprising considering it was probably conversations about polo matches and horse racing that inspired its creation.

In the years following World War I, Gucci founder Guccio Gucci worked as a lift boy at The Savoy hotel in London, serving the city’s elite and carefully noting the nuances of their distinctive style.

Later, on returning to Italy, Gucci combined his experiences of refined style with the company’s saddle-making history, fashioning the first horsebit loafer in 1953 – an iconic shoe that would soon skyrocket the luxury label to stardom.

The design became so iconic, in fact, that Gucci’s horsebit was added to the permanent collection at the Costume Institute at New York’s Metropolitan Museum of Art in the 1960s, and was also the subject of an entire exhibition in 2013 at the Gucci Museo in Florence. Not too shabby for a slip-on.

The horsebit’s central appeal then, as now, is its refinement. Unlike older loafer styles, the horsebit doesn’t look out of place with a formal suit, but completes it instead.

Men's Horsebit Loafers Fashion & Style Outfit Inspiration Lookbook
The best horsebit loafers for men

The Slipper

There once was a time when only two types of men wore slippers outside of the house: Hugh Hefner and your grandad. And really, what’s the difference?

But in recent years, the shoes previously reserved for millionaire playboys and 19th-century aristocrats (Prince Albert was said to be a huge fan) have taken a more louche route, being worn by style mavericks like Ryan Gosling and Kanye West.

As sharp as they are comfortable, the slip-on design is typified by a sturdy leather sole, slight heel and traditional velvet or suede uppers. In addition to being a sleek alternative to the standard dress shoe, slippers can also be used to elevate slightly more casual outfits, especially when sought out in more contemporary leather or neutral colourways.

Regrettably, this invitation is not extended to the shearling-lined moccasins you received at Christmas. Get caught in those at a black tie event and expect fellow guests to stop nothing short of shipping you, and your geriatric get-up, off to a retirement home.

Men's Slipper Loafers Fashion & Style Outfit Inspiration Lookbook
The best luxury slippers for men

How To Wear Loafers

It’s all well and good being able to flex some sartorial muscle and reel off the history of loafers, but incorporating these hard-working, versatile styles into a daily rotation requires a little expert help.

To that end, we tapped stylist Daniel Rhone for his dos and don’ts of loafing around.

Suits You

Celebrated US presidents and famed Hollywood film stars alike have turned to the loafer as something more than a partner to pyjamas. Though, when it comes to tailoring, there is one pertinent rule.

“When wearing a suit with loafers, the most important factor is the length of the trouser leg. The break should be slight […] so that the silhouette appears clean and you can still see the detail of the shoe.”

Men's Loafers With A SuitNext

A Mod-ern Take

Whether gracing the feet of Ivy League prepsters or Camden Teddy Boys, loafers have been worn by a range of men and subcultures, each with their own unique way of styling. Mod fashion likes loafers more than any other style of shoe.

“For a Mod-inspired take on loafers, look for a slim, tapered trouser or a cropped style that delivers a contemporary edge.”

A Men's Mod-inspired outfit with loafersReiss

The Summer Go-To

Equal parts practical and natty, it’s little wonder loafers make for the perfect shoe during the warmer months or while on holiday.

“If looking for an understated but effortlessly cool summer look, team a linen shirt with a pair of light-coloured cotton chinos and a pair of suede tassel loafers.”

Men's Light Chinos and Linen Shirt With Loafers OutfitMassimo Dutti

Go Sockless, The Right Way

As the heat rises, it makes sense to embrace the cooling benefits of baring your ankles by going sockless. However, that doesn’t mean letting feet fly solo.

“Sock specialist Falke produces a fantastic range of no-show socks. Another tip is to dust your feet with a little talcum powder, so you don’t end up perspiring excessively.”

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. 

$110 FROM G.H. BASS

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.

$730 FROM NEIMAN MARCUS

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.

$268 FROM ARTEMIS DESIGN CO.

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). 

$395 FROM ALLEN EDMONDS

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. 

$190 FROM EAST DANE

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. 

$110 FROM SPERRY

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. 

$99 FROM BESPOKE POST

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. 

$158 FROM NISOLO ALEJANDRO

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. 

$560 FROM CROCKETT AND JONES

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. 

$115 FROM FLORSHEIM

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). 

$480 FROM MR PORTER

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