Loafers can be a tricky proposition. Get it right, and you have a sleek, smart pair of shoes for a person of mature and confident character. Get it wrong, and you can end up looking like you’ve just finished a day at school, or auditioned for the panto.
Generally, there are three main types of loafers for men. The most traditional style is the penny loafer, a simply-shaped shoe with a strap of leather across the upper, usually slit in a diamond shape. You usually pair these with smarter outfits – they go especially well with work suits and some formalwear.
The tassel loafer is the penny loafer at the weekend, a softer shape and line with the tell-tale tassels finishing off the look. The horsebit loafer, first made famous by Gucci, adds a metal chain across the top, bringing some more bling to the plainer penny loafer. However, there are plenty variations on the three, including an even simpler slipper style and the grippier driving shoe.
It’s a surprisingly big field, with a wide range of styles to suit most tastes, but one steadfast rule with any footwear is that you get what you pay for. There aren’t any particularly budget shoes on this list; false economy is rife with footwear, and the upper end shoes here, especially from the Northampton-based brands, are almost guaranteed to last you for decades.
After walking a figurative mile in each shoe, and darning our one good pair of socks a few times, we’re pretty confident we’ve found a loafer for almost any occasion.
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Duke + Dexter bowler black loafer
The most versatile loafers on this list, Duke + Dexter’s black loafers, from its opus collection, immediately improve any look you’ve taken more than five minutes putting together, and most that you haven’t. The custom matte black upper has such an elegant sheen that the shoe wouldn’t look out of place with a dinner jacket. The fit and rubber sole stay true to the shoe’s sophistication, but are modern enough that you could pair these with any smart casual look for another level of elegance. The extra-special aspect here is the quilted cotton lining, a padding that makes slipping these on a pleasure.
Buy now £200.00, Dukeanddexter.com
Tricker’s Elton tassel loafer
One of the pricier options on this list, these laid-back loafers are made in the Tricker’s factory in Northampton, home to possibly the finest shoemaking industry in the world. A visit to either the Tricker’s factory or their shop on London’s Jermyn Street will provide you with a bespoke pair of any shoes you could imagine, but their stock of styles is also a premium option for anyone – the Prince of Wales is a fan, if that helps.
The Elton uses the factory’s “ultra-flex” sole construction to make a more formal shoe a weekender, the unlined upper making it fit more like a comfy slipper while maintaining a smart look. The Eltons in earth-toned Castarino suede are a great option for an all-day loafer, but the cherry option adds an extra touch of personality to any outfit. Tricker’s prides itself on making shoes to pass down the generations: these loafers will last you a very long time, and get better with age.
Buy now £425.00, Trickers.com
Fairfax & Favor the bedingfeld II
Fairfax & Favor is a champion of the new generation of shoe producers, and the bedingfeld II is one of its best examples. The colours on the burgundy-tasselled option are particularly pleasing, managing to catch the eye while never feeling “too much”. The loafers’ memory foam inner soles make you forget you’re even wearing them, and are a great investment to the overall quality from the brand. Its side profile is one of the most elegant on this list: it’s a slim and refined shoe that would work in most situations as a safe companion to your outfit, with the quality to outlast anything else in your wardrobe.
Buy now £195.00, Fairfaxandfavor.com
Dr Martens Adrian tassel loafer
First introduced by Dr Martens in 1980, the unisex slip-on loafer has been a mainstay of multiple sub-cultures for 40 years – so much so that, as is invariably the case, it’s wildly popular with mainstream audiences, too. The smooth leather version is stiff when you first buy a pair: a deliberate design decision, giving the wearer the option to keep them as polished as when they were first taken out of the box, or let them scuff and crease for a more lived-in look (the Adrians in cherry red also rub to reveal an undertone). The stylish stiffness doesn’t detract from the comfort, and the thick sole pads your feet brilliantly. Often imitated, never bettered.
Buy now £129.00, Drmartens.com
Crockett & Jones Sydney penny loafer
Another member of Northampton cobbling royalty and Jermyn Street patrons, Crockett & Jones is a classic choice for quality and longevity. You don’t get much more classic than a pair of Sydney penny loafers, either. The last (the mould on which the shoe is shaped) offers a great shape balance between long and round, making it a good choice for businesswear or smart casual settings. The loafer is the most casual style of shoe that you’ll see from most of the high-end shoemakers, but casual doesn’t mean lower quality – there are still hundreds of processes that go into making a shoe like this, resulting in something that will be with you through a fair few job interviews/promotions/your retirement party.
Buy now £450.00, Crockettandjones.com
Penny sports loafer by Arthur Sleep
Handcrafted in London, the most well-known shoes from Arthur Sleep are perhaps the brand’s velvet monogrammed slippers, made to order with any design you wish. However, Arthur Sleep also does a fine line of particularly comfortable “sports” suede loafers, similar to their travel range: they’re just as suited to the promenade as the airport, and will only get comfier with age. The shoemaker whips up its wares to order, and has some big plans in the coming year, so watch this space.
Buy now £300.00, Arthursleepers.co.uk
Grenson booker loafer
Completing the trio of Northamptonshire/Jermyn Street shoemakers, Grenson has a history of making sturdy footwear: it provided thousands of pairs of shoes for the armed forces during both World Wars, and continues to produce shoes with substance. The booker is like a loafer for lumberjacks – strong, with a fantastically chunky sole, but still preppy due to its shape and tassels. The brown washed Nubuck leather brings some subtle brightness to the shoe, which works well with jeans or chinos. Once on your foot, the booker sits snugly and doesn’t feel heavy – a great loafer for the city or a country pub.
Buy now £275.00, Grenson.com
Reiss lex suede loafer
Reiss has made a name for itself in the high-end retail stakes with a strong design ethic and quality materials – and the lex suede loafer is no exception. For us, this is a modern take on the Gucci horsebit loafer, in a more relaxed suede. The bling from the original remains, however, as the bright chain detail elevates the look from the everyday to a bit more of a statement. Socks or no socks, this style is usually one that you either love or would leave alone - we happen to think the lex manages to offer something to everyone.
Buy now £225.00, Reiss.com
Mulo white loafer
Mulo advertises its shoes as being “somewhere between a grown-up skate shoe, deck shoe and a casual loafer”. We can’t think of a better way of putting it: the white loafer is a minimalist dream, with elasticated side panels and a cushioned interior. It feels like a slipper, but has the modern-smart style becoming ever more popular during the weekend. Its considered and clean design is backed up by its high-quality Italian suede upper and lining, which is apt, as wearing a pair makes us feel like we’re on holiday on the Italian coast.
Buy now £145.00, Muloshoes.com
The verdict: Men’s loafers
It’s difficult to choose one pair that stands out from the rest, as the huge variety of loafer styles means that what works for one pair of feet will be anathema to another. However, for a versatile pair of comfortable loafers at a reasonable price, Duke + Dexter’s bowler black Loafers are a strong bet.
For an option that can up your look in a way you hadn’t thought, go for the Dr Martens Adrian tassel loafers - they wouldn’t have been our first choice, but having worn them, they work with a wide range of outfits and are much lighter than expected.
No look is complete without accessories, so take a look at our list of the best men’s belts that will complement any outfit