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The Most Comfortable Shoes Known To Man (Which Aren’t Ugly)

Don’t take another step until you’ve found the shoes that offer cushioning and support without sacrificing style.

Life is hard; wear comfortable shoes. Words to live by, even if they did come from the kind of Instagram post that your great aunt is fond of resharing.

Footwear should be one of life’s red lines – if they don’t fit well, don’t cushion and support your feet, don’t feel like an extension of your extremities, then they’re simply not doing their job. Comfortable shoes are a must.

So what are the most comfortable shoes for men? Well, they’re sneakers, right? No contest, especially compared to stiff formal shoes. The problem is that, even now, in the age of casual dressing and peak sneaker culture, we can’t live in kicks all the time.

Every man needs a pair of smart shoes – for job interviews, for weddings, for those days when you want to feel like a “grown-up”.

So for the purposes of this article, we’re not considering sneakers. Instead, we’re looking for the most comfortable Oxfords and Derbies, the most comfortable loafers, the most comfortable deck shoes and espadrilles.

And that does make things tricky. A boat shoe or an espadrille will always be more comfortable than an Oxford you only roll out for weddings, funerals and dinners with the foreign ambassador. Which is why below you’ll find a mix of brands that create comfortable versions of all styles of smart shoes, plus business-casual footwear you can wear all year round.

The most comfortable shoe brands for men


Sometimes described as the world’s most advanced dress shoes, Amberjack creates hybrid models with the look of a Derby, loafer or Chelsea boot, but the sole of a sneaker.

Unlike a lot of so-called hybrids, the Brooklyn brand hides its techy features well in formal shoes that look good enough for smart offices.

The brand’s athletics-inspired outsoles combine sneaker and hiking shoe materials to offer flexible comfort but support, too.

Inside, a heat-activated memory foam forms to the shape of your feet, while the uppers are crafted from pre-stretched leather, so they feel comfortable from the first wear.


Renowned for its lightweight, crepe-soled desert boots and Wallabies, British stalwart Clarks also makes comfortable shoes in just about every style you can think of.

Combining classic (and formal) designs with clever, spongy footbeds and hidden cushioning elements, you can find Derbies that feel like sneakers and even Oxfords with moulded footbeds and grippy soles.

In the smart-casual range, you’ll also see lightweight, sneaker-style soles on boat shoes, loafers and other slip-ons, while there are extra-wide versions of many of its styles, meaning you don’t have to squeeze into shoes that don’t fit you.

Cole Haan

Smart shoes, but make them athleisure. That’s the unofficial offering from Cole Haan.

The US brand, which was once owned by Nike, combines classic shoe design with sneaker-inspired functional soles and footbeds.

Cloud-like foam outsoles give deck shoes and loafers as much cushioning as a pair of basketball sneakers, and you’ll also find Derbies with lightweight stitched uppers and spongy EVA soles.

Dr. Martens

Once upon a time, Dr. Martens was the go-to shoe brand for postmen, doctors, police officers and other men whose jobs meant they had to be on their feet all day.

We’re not necessarily talking DM’s big stomper boots, but the brand still carries a rich collection of Derbies, loafers and other styles that all benefit from the brand’s stand-out air-cushioned soles and Goodyear-welted construction.

They’re not the lightest shoes you’ll ever wear, but those bouncing soles are famous for a reason. Once you’ve worn them in, you’ll never want to take them off.

Allen Edmonds

One of the most historic US shoemakers, Allen Edmonds has had comfort at the core of everything it does since the beginning.

The company started life creating cork insoles for shoes that helped even the most formal styles mould to the shape of the wearer’s feet. Even on the brand’s high-end Oxford shoes (rumoured to have been worn by more than one US President) you’ll find those cork insoles today.

Elsewhere, you’ll find comfortable driving shoes with rubberised soles, and casual shoe-sneaker hybrids with springy soles for easy wear.


One of the UK’s most celebrated heritage shoemakers, Grenson was founded in 1866, but it’s also a company that has moved with the times.

Staying true to its handmade roots, it nevertheless embraces technology and modern footwear styles to make the most comfortable shoes it can.

The brand’s hiking-influenced Tech line is a good example of its approach, bringing practical elements to some of its classic models. Think Derbies with a rubberised Vibram sole and a padded tongue and collar around the ankle.

Elsewhere in the collection, you’ll find traditional shoes on chunky commando soles, exceptional leathers, a wide range of lasts to choose from and Goodyear-welted construction for extra stability.


With their cork footbeds that mould to the shape of your feet and spongy EVA soles that add a little spring to your step, Birkenstock’s iconic sandals have been summer staples in recent years. But the brand also takes a similar approach to its collection of comfortable shoes.

The contoured footbeds, cork layers and soft suede uppers carry across to Derbies and clog-style shoes, as well as sneakers.

In line with the brand’s laid-back style, the whole collection is designed for casual, easy wear with lightweight materials that hug your feet.


There’s often a little tension between a shoe’s sturdiness and a shoe’s cushioning. Paraboot is one of the brands that gets that balance right, producing hardy, hand-stitched shoes that fit like a second skin.

Its most iconic model, the Michael, is a good example of how Paraboot does things.Within the thick leather upper you’ll find an equally thick and squashy footbed, and the whole thing is built on genuine rubber soles.

The same construction is repeated across the brand’s excellent collection of loafers, Derbies and hiking shoes.


Specialising in casual styles like deck shoes, moccasins and loafers, Sebago makes footwear for people who are on their feet a lot – and need to stay that way.

Its famous Dockside range features soft and supple leather that doesn’t rub when it’s damp, and anti-slip soles that keep you upright on the deck of a ship.

The brand’s moccasins are also worth investing in. Often made from lightweight, easy-wearing suede, this outdoorsy style sits on EVA soles that add cushioning and shock absorption with every step.


Synonymous with laid-back Italian luxury, Tod’s makes comfortable shoes for comfortable lifestyles.

Its most famous design is the Gommino driving shoe, a fine leather or suede slip-on that sits on rubber ‘bubbles’ that cushion every step you take. You can also have the iconic design customised to your tastes and exact fit, for extra comfort.

Those signature bubbles also carry over to the brand’s other lightweight styles, from chocolate suede brogues to ship-shape boat shoes.

With sublimely soft leathers and hardy construction across the collection, it’s no wonder Italian guys always look so chilled (and stylish).

G.H. Bass

The originator of the penny loafer knows a thing or two about easy slip-on shoes that are as preppy as you need them to be, but comfortable too.

The brand’s classic Weejun is a legend of smart-casual style and it’s only getting more comfortable with age, with the addition of rubber or chunky EVA soles on some models.

Elsewhere, G.H. Bass is a reliable provider of moccasins, espadrilles and boat shoes: lightweight slip-on styles that work perfectly with smart summer wardrobes.


Timberland made its name with comfortable work boots that you could labour in all day, while feeling and looking the business. So it won’t be a surprise that the brand also produces a range of comfortable shoes, from hardy nubuck Derbies to commando soled deck shoes.

It also brings the innovative sole units from its work boots to casual and smart-casual shoes. Think responsive EVA soles and footbeds that follow the structure of your feet to maximise comfort and support.

Oliver Sweeney

Goodyear-welted construction and luxury leathers might give the impression that Oliver Sweeney is an arch traditionalist of British shoemaking, and in some ways it is.

It creates hand-made shoes in classic styles that work for the office, weddings and beyond. But the brand also builds comfort into every model.

Its anatomical last follows the form of your foot, and thoughtful touches like an elongated toe or uppers made from a single, stitch-less piece of leather ensures even prim and proper Oxfords conform to your feet.

Then there are modern versions of the classics, like Derbies that sit on lightweight commando soles for extra traction and energy return, or moccasin-style loafers that wrap the leather upper under your foot and above a spongy rubber sole.


More understated Italian elegance from the Macerata region, where Santoni’s founder grew up. The luxury shoe brand creates beautiful loafers and lace-ups, all hand-made in Italy, and with wide fits and generous, rounded toes that make it easy to stay on your feet all day.

As well as traditional leather soles, Santoni creates most styles on comfortable rubber soles, including double monk straps, loafers and Derbies.


With a long history of traditional craftsmanship and boundary pushing innovation (it introduced the concept of right and left shoes, for example), Church’s is one of the most celebrated shoemakers to rise from the UK’s Northamptonshire footwear industry.

And in amongst the exceptional Oxfords and Chelsea boots, you’ll find modern takes on classic designs that add comfort and functionality.

The brand’s Urban Crossover range, for example, introduces lightweight but chunky rubber soles for extra traction and support on city streets. And even its traditional formal shoes will fit perfectly once you’ve worn them in.

What makes shoes comfortable?


Man wearing chunky sole Clarks loafers with white cropped pants


The most comfortable shoe in the world is the one that fits your foot perfectly. Make no concession to fit, not ever.

And we don’t just mean standard sizes. Look for brands that offer wide fits or half sizes if you need them, or traditional shoemakers that provide detailed breakdowns of the lasts they build their different models on.


The comfortable inner sole lining of a Tod's shoe


Gone are the days of formal shoes offering an unforgiving plank under foot. Today’s footbeds are informed by what we know about orthopaedics, and borrow cushioning and other build features from sports shoes and hiking boots.

Think EVA-moulded footbeds that support the contours of the foot’s anatomy and cushion every step.

Sole unit

Close up of a suede Oxford wingtip Cole Haan shoe with a comfortable rubber sole

Cole Haan

Like the footbed, the soles of modern formal shoes have come a long way since the days of tough and unyielding leather foundations. Today’s soles can be made of rubber, plastics and polyurethane, which offer varying degrees of cushioning, grip and shock absorption.

Depending on the style of shoe, you’ll also find commando-style soles for extra stability or sneaker-inspired soles for an added spring in your step.

Toe style

Pair of men's black commando sole chunky Derby shoes


If you can bear to, study your toes. Are they wide? Uniform? Do they taper down? Let the shape of your toes influence the style of shoe you go for.

Oxfords tend to be narrower at the toe, while loafers are squarer. A Derby is usually somewhere in the middle.


Man wearing a pair of Tod's shoes lying on a bed while woman has bath in background


Maybe there’s a formula for working out what the perfect weight of shoe is, but we don’t know it. Lightweight footwear is generally more comfortable, especially on early wears, but when it comes to formal styles, that can mean thin leathers, insubstantial soles and shoddy construction.

In our experience, the most comfortable shoes aren’t necessarily the lightest. Extra weight should offer more stability, support and long-term wear.


Man holding luxury brown leather tassel loafer while wearing khaki pants and black shirt

Allen Edmonds

Leather has, for centuries, been the material of choice for smart footwear. It’s tough but pliable, practical but polished. Today, however, there’s a decision to be made between leather, vegan-friendly leather alternatives and even modern fabrics like knitted polyurethane.

If you opt for hardy leathers, you also have to consider the breaking-in period. Some of the most comfortable shoes for men feel like a medieval form of torture for the first few wears, as they slowly mould to the shape of your feet.