Most Comfortable Dress Shoes for Men

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Unlike most websites that compile such lists, this article is written by a trained shoe-maker. Therefore, we know that the term ‘dress shoe’ does not apply to all the shoes on this guide. At least not in a strict sartorial sense.

There are several shoes on this list that pass as ‘proper’ dress footwear. Like the Florsheim Midtown, Clarks Un Tailor Tie, and Rockport Big Bucks Margin, for example.

On the other hand, shoes like the Cole Haan Grand Ambition Wingtip and Johnston & Murphy Holden are dress sneakers that go better with jogging-style pants rather than pleated trousers cut of super-130s cloth. Perhaps ‘officewear’ is a fitting description of these shoes.

We have experience making dress shoes by hand – the old school way. That means starting with a basic sketch and then drawing on a masked shoe last, followed by cutting patterns and size grading.

We’ve also cut fine grain leather and skived the edges so that they fold easily without the bumps. We’ve stitched dress shoes and lasted them manually by pulling the edges with a pair of pliers and then hammering over them.

We’ve made blocked leather heels too, by gluing, grinding, painting, and polishing different layers of leather. We’ve built Goodyear-welted shoes too – the gold standard of upper and sole attachment.

And what, exactly, is the point of this seemingly irrelevant technical rant?

If there’s one thing that making dress shoes has taught us, it’s that they are not comfortable. Not when you compare them to the modern athletic sneaker.

The traditional dress shoe design and construction haven’t changed in over a century. Dress shoes were born in an era when terms like ‘foam’ or ‘cushioning’ did not exist.

Vintage dress shoes were made almost entirely (save for a few Cork bits) of leather, and that created an extremely stiff fit and feel. A break-in period wasn’t optional. Much like the manually-wound wristwatch, all-leather dress shoes are an anachronism.

The sole cushioning of an authentic dress shoe feels like a piece of wood. Some leather dress shoes also use metal shanks that light up the security detectors at an airport. If that wasn’t bad enough, all-leather outsoles grip terribly on smooth floors when new.

Even the rubber soles used on British dress shoes – like the venerable Dainite sole for instance – aren’t very comfortable. While they grip better, the cushioning is hard as a rock.

The generalization also applies to slightly (more) informal footwear like Chelsea boots or loafers that are produced using dress shoe construction techniques. A picture speaks a thousand words, so here are a few examples that illustrate our point.

So this guide isn’t about dress shoes with an all-leather construction and a Blake-stitched sole. It’s about easygoing office shoes that combine old-school traditionalism with comfort derived from the sports shoe industry.

Sometime during the ’80s, office-wear shoes went through a rapid transformation due to the introduction of Polyurethane and rubber soles. This allowed the upper to retain its classic design while offering noticeable comfort-oriented improvements.

Brands like Clarks, Florsheim, Mephisto, and Rockport have been selling comfortable dress shoes for several decades. Many of their products combine formal silhouettes with rubber or foam midsoles – a design that makes walking or standing comfortable. A cushy foam-lined footbed is often part of the package.

The second wave of innovation came a decade ago, one that led to an exponential upside in dress shoe comfort. The change can be traced to a single brand – Cole Haan. The brand was then owned (not anymore) by Nike, which in its usual enthusiasm, decided to mate a boring Wingtip Oxford with a Lunarlon midsole.

Back then, Lunarlon foam was used in many Nike running shoes. All of a sudden, there arrived a product with the aesthetic of a dress shoe and the ride comfort of a running sneaker.

It was called the Cole Haan LunarGrand Wingtip, and its contrast color midsoles spawned a thousand imitations. Today, office-friendly shoes with comfortable EVA midsoles and soft insoles are a ubiquitous sight, so this is a great time to write this buyer’s guide.

We’ve curated nearly a dozen models from the hundreds of available options using the following filters. We do this for every guide so that you can explore other options outside our recommended list.

1) Non-leather soles: All the models featured here either have rubber, Polyurethane (PU), or EVA midsoles. Besides adding comfort, the foam midsoles help reduce the weight.

This is why brands like Allen Edmonds and Carmina are excluded.

2) A comfortable footbed: A soft insole is essential for step-in comfort. Shoes like the Florsheim Midtown and Clarks Un Tailor Tie have removable Ortholite insoles that can be substituted with a custom orthotic.

Ideally, the insole should have a contoured profile that supports the arch. This is another feature that’s inspired by performance footwear design.

3) Preferably leather-lined interior or footbed: A leather-lined footbed elevates the fit and ride comfort.

4) Leather uppers in a traditional silhouette: That’s because mesh shoes stray into the casual shoe category. We may well as make a running shoe guide then.

5) Folded tongue flap: Whenever possible, look for a dress shoe with a soft, folded tongue and foam padding. This prevents the tongue from biting into the foot, thus minimizing the break-in period.

6) Safe colors: If you think that the colors on this guide are boring, that’s because you’re right. Most workplaces with a formal dress code will frown on sneaker-type colors. So this is a ‘black and brown’ shoe guide.

7) No luxury dress shoes: Except for Mephisto, most shoes range between $130-200 here – much cheaper than brands such as Crocket and Jones, John Lobb, or Santoni that can easily cost north of $600. We’ll probably do a luxury shoe guide in the future, but those products are off-menu for now.

8) Additional features such as waterproofing: A water-repellent upper comes in handy during winter rains or spring showers. Wherever applicable, we’ll call that out in the product description. On this guide, only the Ecco ST1 Hybrid Gore-Tex is waterproof.

This guide contains various dress shoe silhouettes, so here’s a quick style primer. A Wingtip Brogue is the most formal, followed by plain or cap toe, and finally sporty dress shoes with foam midsoles. Your choice should be based on how conservative (or not) the workplace setting is.

Our pick would be shoes from either Clarks, Florsheim, and Ecco – they offer an excellent balance between decent, if not great, construction, along with ride comfort and additional features such as waterproofing.

If not for the weatherproof elements, we’d pick either the Florsheim Midtown Cap Toe or Clarks UnTailor Tie. These relatively affordable shoes offer excellent comfort and use nice materials and construction techniques.

For all-weather use, we recommend the Ecco ST 1 Hybrid Gore-Tex. It’s got everything – a comfortable ride, dressy upper, waterproofing, and a removable footbed that’s lined with leather.

As much as we like the styling of Cole Haan and Johnston & Murphy, their build quality and materials aren’t that great for the price. Some of their more expensive products are still good, so it’s important to know which ones to buy.

The shoes are sorted in the order of recommendation, and the links to our in-depth reviews are also included.

1) Florsheim Midtown Cap Toe

This cap-toe Derby is another variant that’s based on the same fit and midsole as the Florsheim midtown plain toe. It’s a classic design that blends into most formal settings.

Like the Clarks Un Tailor Tie (next shoe on this list), this shoe follows most of the best practices that make a dress shoe comfortable.

Noteworthy features would be the non-slip TPR (Thermoplastic rubber) sole that delivers traction and comfort, as well as a leather-lined Ortholite footbed that adds a layer of step-in comfort.

The interior is the most comfortable on this list, thanks to the soft ‘Suedetec’ lining and supple leather that’s sourced from environmentally responsible tanneries. The fit and finish of the leather upper is excellent for the price.

The Midtown Cap Toe, along with the Clarks UnTailor Tie, is one of the dressiest shoes on this guide. Unlike modern dress sneakers, the dark-colored and heeled sole has very traditional styling. This is as close as it gets to a dress shoe; our in-depth review of the Midtown is here.

If you prefer a plain toe version, that’s also available to buy.

2) Clarks Un Tailor Tie

As a simple yet comfortable office shoe option, the Clarks Un Tailor Tie is a basic Derby-style silhouette that is suitable for most workplaces.

Large panels of corrected-grain leather keep the aesthetics clean, while the leather-lined tongue and collar create a comfortable interior environment.

There is a reason why we have featured the Clarks Un Tailor Tie at the top. This shoe embodies the essence of this guide – this is truly a comfortable dress shoe that’s loaded with design best practices.

Making the ride comfort happen is an EVA sole and a removable Ortholite insole with a leather footbed and contoured shape. The upper relies on several comfort-oriented features like a folded tongue, leather lining, and a true-to-size fit.

This is our top pick on this guide. It’s lightweight, well-fitting, cushioning, affordable, and uses quality materials. It’s hard to go wrong with this shoe; our full review is here.

3) Ecco ST1 Hybrid Brogue Tie

This is an Ecco, so everything about the shoe feels like quality. The Wingtip Brogue upper is made out of premium corrected-grain leather, and the insides also get the lux treatment.

The lining is leather, and so is the surface of the foam-backed insole – these treatments make the interior smooth and comfortable.

As with most Ecco shoes, the cushioning is based on a resilient Polyurethane core with a cushioning center. A soft thermoplastic rubber outsole adds grip and comfort to the ride quality.

A word of caution about the upper fit – the sizing fits narrow, so try before you buy. Getting a half size larger may be in order.

The Gore-Tex version of the ST1 Hybrid Plain toe (next on this list) is our top waterproof dress shoe pick. The GTX and standard ST.1 Hybrid share the same midsole and footbed, so our review is worth reading.

4) Ecco CityTray Gore-Tex

Ideally, we would have liked to have featured the waterproof Gore-Tex variant of the ST.1 Hybrid for rainy commutes. Not many dress shoes have a Gore-Tex lining, and fewer have a comfortable midsole like the ST.1.

However, the ST.1 Hybrid GTX no longer appears to be available, so the Ecco CityTray GTX is the next best thing. From the outside, it’s hard to tell that this is a waterproof dress shoe; it looks exactly like the standard CityTray.

The leather used on the upper is supple and comfortable, whereas materials like the mesh and leather lining make the interiors smooth. The removable insole has a leather-lined footbed for underfoot comfort.

Like most Ecco shoes, the City Tray uses a Polyurethane midsole that’s directly attached to the upper. The traction is delivered by the built-in texture of the integrated outsole.

5) Cole Haan Grand Ambition Wingtip

The Cole Haan Grand Ambition series is new for the season, and so far we see a Wingtip, Derby, Chelsea, and Chukka uppers on a shared EVA foam midsole. For this guide, we chose the Wingtip version for its dressier styling.

This is one of the better shoes in Cole Haan’s assortment. The welted upper sits on a dual-density EVA foam midsole that also forms the outsole.

A fabric-lined footbed (non-removable, but can be detached with some effort) adds some softness over the midsole. Together, the foam layers make the ride comfortable enough for all-day wear.

The dark sole color blends well with the burgundy upper to tone down its dress sneaker overtone.

Speaking of Burgundy, the Grand Ambition Wingtip’s upper is clearly inspired by the Oxblood Cordovan color #8. But the leather is merely a corrected-grain cowhide with fancy Brogue and laser-etched details. While the heel collar isn’t padded, the soft synthetic lining makes the fit smooth and comfortable.

All in all, this is a sharp-looking pair of shoes with plenty of lightweight ride comfort. Our wear-tested review can be found here.

6) Rockport Big Bucks Margin

This basic Rockport Derby has a rather peculiar name for a dress shoe. But if you look past the verbiage, then there’s little to complain about. And contrary to its name, this model doesn’t cost big bucks.

A smooth leather upper in a Derby plain toe keeps things simple yet dressy on the outside; a Polyurethane midsole adds ride comfort without the weight penalty.

7) Cole Haan OriginalGrand ShortWing

Cole Haan is the creator of the modern ‘athletic fusion’ category, and the OriginalGrand silhouette is its most vocal advocate.

A leather upper in a wingtip brogue styling gives the Originalgrand all the dress-shoe legitimacy it needs. The decorative Welt on the edges is attached to a full-length foam midsole with a token placement of outsole rubber.

It’s worth mentioning that this version no longer has the Lunarlon foam since Nike broke up with Cole Haan.

Having said that, the midsole still packs a generous amount of cushioning for a dress sneaker. Though an all-black color is pictured here, sportier versions with contrast midsoles are also available.

And here’s our full review of this dress sneaker.

8) Rockport Garret Plain toe

By marrying a subtle nubuck leather upper with a sneaker-like midsole, the Rockport Garrett Plain Toe channels its inner Cole Haan.

The tonal stitching and plain toe silhouette helps the Garett blend into formal office environments, while the EVA foam midsole and removable insole provide all-day comfort.

The contoured EVA foam footbed is lined with soft textile for comfort, and the foam midsole keeps the weight low. Both the heel and tongue are padded for interior comfort; the waxed laces are a nice touch.

9) Cole Haan Zerogrand Wing Oxford

The ZeroGrand Wingtip is lighter, sportier, and more flexible than the OriginalGrand Wingtip. The midsole is inspired by Nike Free, a design that makes it extremely flexible and comfortable.

Sure, the distinctive midsole takes away a bit of the formal dressiness. But this is 2021, and a shoe like this aligns perfectly with the work-from-home dress code.

There’s a softer foam core inside the flexible midsole for enhanced cushioning. This is the lightest shoe on this guide by far. We recommend reading our in-depth review of the Zerogrand.

10) Mephisto Marlon

There’s nothing groundbreaking about the Mephisto Marlon, and that’s part of its charm. Its $400 MSRP gets you premium quality materials all around, be it the leather-lined interior or premium tumbled leather upper that’s welted to the natural latex rubber sole.

The pebbled Derby-style exterior isn’t the dressiest, but will fit into most formal and semi-formal environments.

11) Johnston and Murphy Holden

The J&M Holden Wingtip is a comfortable dress shoe with a smooth sheepskin-lined footbed. The upper interiors are lined with foam-quilted leather for a smooth over-the-foot feel. The Holden doesn’t have a ‘Dual width’ insole like how some J&M shoes do, but the upper fits true-to-size.

The midsole and outsole are a part of a foam monosole that delivers excellent cushioning for all-day comfort.

There are multiple color options available; both in contrast and tonal-colored combinations. Needless to say, the Holden models with tonal midsoles are dressier than the contrast-colored variants.

On a related note, the ‘welt’ you see on the midsole isn’t a true welt. The leather upper is pasted to the midsole; the latter has pre-attached welts for decoration. Read our full review of the J&M Holden here.