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 – sometimes a little samey – holy footwear trinity of brogues, Derbies and Oxfords, loafers are often hugely underrated, written off as flamboyantly ‘dandy’ or too difficult to pull off with any real degree of success.

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 numbers – there’s something to suit every taste.

Material Matters: Leather Or Suede?

Before delving into the types of loafer you should be considering, 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, each with its own strengths and weaknesses.

With their sleek and gleaming finish, leather loafers make for the perfect punctuation mark for smarter looks, whether a full suit or smart-casual tailored separates combination. Although you’ll want to be sure you 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 your footwear – be exclusively reserved for the spring/summer months. Their luxurious but delicate finish means suede loafers should be protected from moisture at all costs.

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

The Penny Loafer

Irrepressibly smart, the penny loafer is the preppy footwear classic that still takes pride of place on our shoe rack 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, dubbed the ‘Weejun’ (sounding like Norwegian), adding a strip of leather across the saddle 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 of G.H. Bass & Co. “Our Weejuns have been adopted by many subcultures and trends throughout the years.”

While it’s true pennies will work for smarter attire like summer suiting, they’re best used to add some 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 Outfit Inspiration Lookbook

J CREW 2015SCOTCH & SODA AMSTERDAMS BLAUW FALL 2014office shoes ss13tommy hilfiger tailored ss14scotch & soda ss15mango man winter 2013jaeger ss13J CREW 2015J CREW february 2015de fursac ss14tommy hilfiger tailored aw14boss hugo boss ss15

Best In Class: G.H. Bass & Co

GH Bass Larson Penny Loafers, available at ASOS, priced £125.

GH Bass Larson Penny Loafers

Alternative Styles

  • Selected Homme Ley Suede LoafersSelected Homme Ley Suede Loafers
  • Asos Loafers In LeatherAsos Loafers In Leather
  • Topman Tan Leather Penny LoafersTopman Tan Leather Penny Loafers
  • John Lewis Lloyd Suede Penny Loafers ChocolateJohn Lewis Lloyd Suede Penny Loafers Chocolate
  • AglianoAgliano
  • J. Crew Kenton Suede Penny LoafersJ. Crew Kenton Suede Penny Loafers
  • DesDes
  • Rs Pembrey R Penny Loafer ChurchRs Pembrey R Penny Loafer Church
  • Bass Weejuns Logan Leather Penny LoafersBass Weejuns Logan Leather Penny Loafers
  • Churchs Suede Penny LoafersChurchs Suede Penny Loafers
  • Churchs Suede Penny LoafersChurchs Suede Penny Loafers
  • Gucci Burnished-leather LoafersGucci Burnished-leather Loafers

The Tassel Loafer

Although ‘tasselled loafer’ may in some places be a pejorative for ‘lawyer’, the style first came about thanks not to an attorney but an American actor 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 and – the story goes – at some point during the 1940s 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 tassel 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 tassel style featuring distinctive foxing (i.e. 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 $700 for a pair by Brooks Brothers.

Men's Tassel Loafers Outfit Inspiration Lookbook

gant rugger ss15massimo dutti nyc 5th avenue ss15Hickey Freeman ss16j crew july 2015dunhill ss15reiss ss15next 2015Brunello Cucinelli ss16sarar ss15bagozza ss15baldessarini ss15massimo dutti december 2013

Best In Class: Brooks Brothers

Cordovan Tassel Loafers, available at Brooks Brothers (US), priced $690.

Brooks Brothers Cordovan Tassel Loafers

Alternative Styles

  • H By Hudson Pierre Tassel LoafersH By Hudson Pierre Tassel Loafers
  • Reiss Pete Tasselled Loafers BlackReiss Pete Tasselled Loafers Black
  • J. Crew Ludlow Suede Tassel LoafersJ. Crew Ludlow Suede Tassel Loafers
  • Topman Brown Suede Tassel LoafersTopman Brown Suede Tassel Loafers
  • Topman Navy Suede Tassel LoafersTopman Navy Suede Tassel Loafers
  • Bass Weejuns Tassel Loafers In BrownBass Weejuns Tassel Loafers In Brown
  • Bass Weejuns Leyton Tasselled Leather LoafersBass Weejuns Leyton Tasselled Leather Loafers
  • Burton Montague Burton Premium Grey Tassel Leather LoafersBurton Montague Burton Premium Grey Tassel Leather Loafers
  • Grenson Scott Tassel Loafer Tan Grain LeatherGrenson Scott Tassel Loafer Tan Grain Leather
  • River Island Brown Leather Slip On Tassel LoafersRiver Island Brown Leather Slip On Tassel Loafers
  • Layton Moc Kiltie Loafer Bass WeejunsLayton Moc Kiltie Loafer Bass Weejuns
  • Dune Remy Tassel Suede Loafers GreyDune Remy Tassel Suede Loafers Grey

The Horsebit Loafer

With bluer blood than its brother styles, the horsebit loafer is the definitive dress loafer – and no brand does them better than luxury Italian label Gucci.

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 WWI, 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 after skyrocket the brand to stardom.

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 shoe.

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 Gucci Horsebit Loafers Outfit Inspiration Lookbook

Gucci Spring 15Gucci SS13Gucci SS13

Best In Class: Gucci

  • Gucci Suede Horsebit LoafersGucci Suede Horsebit Loafers
  • Gucci Horsebit Leather LoaferGucci Horsebit Leather Loafer
  • Gucci Softy Roos Horse Bit LoafersGucci Softy Roos Horse Bit Loafers
  • Gucci Horsebit Grained-leather LoafersGucci Horsebit Grained-leather Loafers
  • Gucci Horsebit Leather LoafersGucci Horsebit Leather Loafers
  • Gucci Horsebit Leather LoafersGucci Horsebit Leather Loafers

How To Wear

So, how can you start incorporating these hard-working, versatile styles into your daily rotation? We tapped Topman personal shopper Daniel Rhone for his dos and don’ts:

“When wearing a suit with your loafer, the most important factor is the length of your trouser leg; the break should be slight at the top of your loafer so that the silhouette appears clean and you can still see the detail of the shoe.”

Men's Loafers With A SuitImage: Mango Man AW14

A Mod-ern Take

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

A Men's Mod-inspired outfit with loafersImage: J.M Weston SS15 Campaign

The Summer Go-To

“If you’re 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 OutfitImage: Massimo Dutti NYC SS14

Go Sockless, The Right Way

“During the summer you should embrace baring your ankles by going sockless. 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 in your brand new loafers.”

Accessories you need to go sockless


Final Word

Whether gracing the feet of Ivy League prepsters or Camden Teddy Boys, celebrated US presidents or famed Hollywood film stars, the loafer has come a long way from its humble origins. Equal parts practical and natty, it’s little wonder this shoe’s popularity continues to endure across the board.

So are you a tassel or horsebit kind of guy? Or perhaps the simply styled penny wins your vote?

Let us know below.