Fashion Men's Fashion

What Are The Most Comfortable Smart Shoes For Men?

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Some days – for work, a function or just because you feel like it – you need to dress up. But there’s always that hesitation in having to don dress shoes – so often stiff, uncompromising and hard on your tootsies. At least, that was the case.

More relaxed dress codes, as well as the introduction of new technologies and ways of making shoes, mean you don’t have to be in pain for your style any more. Today, you can take a stand in shoes that won’t leave you bleeding and blistered, and you’ll still look the part.

Whether you opt for a shoe brand with an established reputation for comfort, are ready to play the longer game and break in a classic Goodyear welted pair, or opt for a more trainer-inspired, hybrid style, comfortable dress shoes are there to let you walk without wincing.

What Is A Dress Shoe Today?

A dress shoe used to be rather limited in style. For most men, well into the late 20th century, dress shoes meant dark (which really meant black), plain Oxfords – a slim-line lace-up largely free of decoration, with the exception perhaps of some light broguing. Buckles were out (too fancy). Loafers were out (too casual).

But with the shift in attitude towards office wear, smart shoes have also loosened up, at least in the styles available. It still largely rules out sports shoes or the likes of work boots, but the scope now includes monk shoes, Chelsea boots and chunkier looks of the kind that once would have been worn more for walking the dog.


“Men dress differently now, even when dressing up. You might wear shoes that contrast with your suit, for example,” says William Church, co-owner of Joseph Cheaney shoes, where sales of black dress shoes have fallen over recent years. “Colours the likes of chestnut and burgundy, or with burnishing – there are many more options. The possible details are almost endless and there’s room for quirkiness.”

Even hybrid models – a dress upper on a trainer or work boot-derived outsole – are possible for semi-formal dressing. Of course, if the occasion calls for properly formal dressing, do respect that: think shoes not boots, lace-ups not slip-ons, dark high-shine leathers, a slimmer silhouette and low profile (rubber or leather) sole.

How To Find Comfortable Dress Shoes

Generations that have come up wearing trainers have different – and sometimes unrealistic – expectations as to how comfortable a dress shoe might be. A new pair of Oxfords is never going to feel as cloud-like underfoot as a new pair of AirMax, which are built for lightness and ease of movement.

Even so, there are things you can look out for to ensure a comfy smart shoe.

Pick The Right Style

While traditionally a dress shoe would have been an Oxford, there are numerous smart styles available today that do the job just as well. The nature of an Oxford’s lacing system means there’s ample chance of pinching around the toes and the top of the foot. The same can be said of loafers, which need to be snug to ensure they stay on your feet. More relaxed is a Derby shoe, which has the vamp sewn over the top, increasing flexibility. If you’re on your feet all day, go for the latter.

Do Some Sole Searching

Greater efforts are being made to build comfort into work shoes: rubber soling (relative to leather soles) reduces impact on the heel, where most downward pressure is felt; some models now use a layer of memory rubber padding under the branded liner to further reduce impact – a step up from the previous material typically used, which tended to compress over time and stay compressed.

Traditional shoemakers will also argue that Goodyear-welted construction, although not modern, remains extremely comfortable – each shoe has a cork bed that moulds itself to your unique foot. You just have to be prepared to go through the breaking in process.

Check Your Leathers

Softer leathers are available too – though note that these are not as hard-wearing. Unlined leathers and suedes are readily accessible, and offer superior pliability and comfort when walking. In some cases there won’t be much of a break-in period at all, which is good news if your pain threshold isn’t up to scratch.

Know Your Shoe Size – And Shape

Yes it’s all well and good knowing your shoe size – although it will vary from brand to brand. Many shoes are now offered in different widths too, so if you often find the sides of your feet pinching, go for something wider next time to accommodate all that real estate. Also check the shape if your foot, says Church.

“Certainly one advance of the changes in dress shoes is that men don’t just have to wear that standard slim-line, refined shape of shoe,” he notes. “Men are freer to wear different last shapes and, crucially, to wear the one that best suits their foot shape. Before any decision is made about style, find the right last shape for you. It really is essential to comfort.”

Grin And Bear It

A high quality calf leather – of the kind long used in traditional upmarket shoemaking – may initially be stiffer, but best absorbs moisture away from the foot, which can be a key factor in overall comfort (not to mention foot health and the longevity of the shoes). Wear a thick pair of socks and break them in around the house before subjecting yourself to a painful commute.

Crockett & Jones CamdenCrockett & Jones Camden

Go-To Brands For Comfortable Dress Shoes


The Northampton shoemaker, best known for its chunky ‘country’ brogues, also offers a line with what it calls an ultra flex sole – still leather on the insole and sole but some 30 percent lighter than comparative models. Rufus, a suede monk strap shoe in brown or navy, is the dressier of the styles.

Buy Now: £395.00

RUFUS shoe

Mr. P

Online retailer Mr. Porter carries a wide range of styles but its own brand shoes lean more towards the semi-smart, affording them a greater emphasis on obvious comfort benefits the likes of a rubber lug commando soles, flexible suede uppers or, on its Lucien desert boot model, soft half-lined uppers with crepe soles.

Buy Now: £375.00

MR P. Jacques Leather Derby Shoes


The problem with shoe brands that put comfort first is that the results are often pretty ugly – they’re all tech and no style. But that’s not always the case. Comfort footwear specialists Mephisto, for example, packs a lot into a plain, simple, suit-friendly package: its Marlon model, for example, comes with an air cushioned sole and the brand’s proprietary Air Jet system, which allows air to flow through the shoe with each step.

Buy Now: £220.00



With its long history of making children’s shoes, with fit and comfort inevitably to the fore, Clarks has translated this ethos into its shoes for the grown-ups. Even conservative black toe-cap styles get a comfort overhaul, with a lightweight EVA sole unit and Clarks’ “anatomically targeted dual density” Cushion Soft technology, which cuts down strain felt on the ball of the foot.

Buy Now: £75.00

Un Aldric Cap

Joseph Cheaney

Traditional English shoemaker Cheaney places the emphasis on comfort through a Goodyear welted construction, though it also includes in its collection a number of dress styles on rugged commando outsoles. In its Bertie style it even offers what might be called a dress sandal – a smart T-bar bucking shoe with aerating cut-outs along the upper.

Buy Now: £365.00

CHEANEY Deal Derby in Mahogany Grain Leather

Dr. Martens

Its Airwair sole might have redefined comfort when it was launched in the 1950s, but Dr. Martens is best-known for its clumpier shoe styles beloved, once upon a time, by police and postmen. But don’t rule it out for dress shoes. It’s about selecting a style free of the signature yellow stitching – the likes of the Adrian Arcadia fringe loafer or cherry red Arcadia brogue.

Buy Now: £120.00



The eventual comfort of a Goodyear welted construction need not imply an out-and-out classic shoe style. New York-based brand Feit, for example, takes a familiar build and shape, but puts a contemporary spin on the details – its black Braided Oxford model, for instance, is a whole-cut made with a one-piece veg-tanned leather upper, with an ornamental tassel at the heel.

Buy Now: £629.34



Grenson has made a name for itself by pushing stronger takes on traditional shoe styles, many of which are built around lightweight, cushioning wedge sole units. But it also pushes at the edges of dress shoe acceptability with its trainer hybrids the likes of its Sneaker 3, a brogue calf leather upper on a sneaker sole unit.

Buy Now: £190.00

Sneaker 3

Crockett & Jones

Although another Goodyear-welted shoe manufacturer, Crockett & Jones reflects the growing demand for comfort across a number of styles, from those with highly flexible crepe soles to rugged yet smart suede boots with Dainite rubber soles. For slipper-like comfort, consider Genoa, a super-soft, rubber-soled penny loafer driving shoe, for semi-smart summer style.

Buy Now: £220.00

Genoa Dark Brown Antique Calf

Cole Haan

Classic US brand Cole Haan has won a reputation for the comfort of its dress shoes. A standard brogue on the outside, such a style might, for example, on the inside have an anatomical footbed and heel – which adjusts weight distribution – flexible outsole and moisture-wicking textile lining. Why suffer for your style?

Buy Now: £160.00

Black Jefferson Grand Wingtip Oxford Shoe

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