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Most Comfortable Dress Shoes for Men

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What’s the best way to break out of a running shoe content rut? Write about dress shoes, obviously. And not just any dress shoe – but the ones which combine old-school traditionalism with comfort derived from running shoe technology.

Unlike most websites that compile such lists, this article is written by a trained shoe-maker.

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 bumps. We’ve stitched dress shoes and lasted them manually by pulling the edges with a pair of pliers and then hammering over.

We’ve made leather soles too, including grinding, painting, and polishing. We’ve Goodyear Welted shoes too – the gold standard of upper and sole attachment.

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

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

The traditional dress shoe design and construction hasn’t changed in over a century – a form factor where terms like ‘foam’ or ‘cushioning’ do not exist. Dress shoes were made almost entirely (save for a few Cork bits) of leather and delivered an extremely stiff fit and feel which required a break-in time.

And as far as the sole cushioning was concerned, dress shoes felt like a piece of wood – many still do. Also, some leather dress shoes still use metal shanks which lights up security detectors at airports. The grip of all-leather outsoles is terrible on smooth floors too.

So this guide isn’t about dress shoes with an all-leather construction.

Sometime during the ’80’s, dress shoes went through a drastic evolution due to the introduction of Polyurethane and rubber soles. This allowed the upper to retain its classic design while offering a significant improvement in ride comfort and weight.

Brands like Clarks, Mephisto, and Rockport have been selling comfortable dress shoes for the last couple of decades. Many of their products combined formal silhouettes with rubber or foam midsoles – a design which made walking or standing comfortable. A soft foam-lined footbed was often part of the package.

The second wave of innovation came seven years ago, one which led to an exponential increase 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 Wingtip Oxford with a Lunarlon midsole.

Back then, the rubber-EVA Lunarlon foam was used in many Nike running shoes. So suddenly, you had a product which had 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. Dress shoes with comfortable EVA midsoles and soft insoles are a common sight now, so this is a great time to write this buyer’s guide.

We’ve distilled a dozen models from hundreds of available options using the following filters. We do this for every guide so that you can explore other options not mentioned here.

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

2) A comfortable footbed: A soft insole is essential for step-in comfort. A few models on this guide have removable insoles that can be substituted with a custom orthotic.

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

4) Majority leather uppers and traditional silhouettes: While there’s one shoe here with a mesh-leather combo, the rest are all leather. Else, non-leather shoes start straying into the casual shoe category.

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

6) No luxury dress shoes: Except for the Mephisto, most shoes range between $130-200 here – much lower than the brands such as Ferragamo, Hermes, John Lobb, or Hermes which can easily cost north of $500.

7) Additional features such as waterproofing: We kid you not – as we type these words, it’s raining outside. So a water-repellent upper comes in handy for winter rains or spring showers. Only some of the models below have waterproofing, so we’ll call that out in the description.

You’ll come various dress shoe silhouettes on this guide, so here’s a quick tip. A Wingtip Brogue is the most formal, followed by plain toe, Faux Moc with a stitched Apron, and finally sporty dress shoes with contrast color midsoles. Your choice will depend on how conservative (or not) the social setting is.

Our pick would be Johnston and Murphy models – they offer an excellent balance between premium construction, ride comfort, and additional features such as waterproofing.

The shoes are sorted alphabetically.

1) Clarks Un Tailor Tie

If you want a simple yet comfortable dress shoe, the Un Tailor tie-up should be on your radar. This is a basic Derby style silhouette which is suitable for most workplaces.

Large panels of full-grain leather keep the aesthetics clean, while the leather-lined tongue and collar make the interiors comfortable.

The ride is fairly cushioned for a dress shoe, thanks to the molded Ortholite insole over an EVA foam and rubber midsole.

2) Cole Haan OriginalGrand Wingtip Oxford

Cole Haan was the originator of the ‘athletic fusion’ category, and the OriginalGrand Oxford is its standard-bearer.

A premium leather upper fashioned in a wingtip brogue gives you all the dress-shoe cred you need. The Goodyear Welt on the edges attaches to a full-length foam midsole with a token placement of outsole rubber.

Admittedly, this version no longer has Nike Lunarlon since Nike broke up with Cole Haan. But still packs a generous amount of cushioning for a dress shoe. Though an all-black color is pictured here, sportier versions with contrast midsole are also available.

Also see: The Cole Haan ZeroGrand Laser Wing Oxford

3) Cole Haan Zerogrand Wing Oxford

The ZeroGrand Wingtip is lighter, sportier, and more flexible than the OriginalGrand Oxford. 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 2019, and a shoe like this pairs perfectly well with a suit.

4) Dockers Hawking Smart Series Oxford

This shoe’s name is quite the mouthful, we know. With a mesh and leather upper combo, the Dockers Hawking is borderline casual shoe territory. Its wingtip silhouette is the only reason why this shoe exists on this list. This is more of a casual Friday dress shoe – if you know what we mean.

The upper is treated with a stain-repellent coating so that liquids bead right off. The fit and ride comfort comes from the stretchable textile upper, a molded foam insole, and an EVA midsole. The Dockers Hawking has a sub-$100 retail price; that makes it the most affordable on this list.


Also see: The New Balance 1100.

5) Ecco ST1 Hybrid Plain toe

This is an Ecco we’re talking about, so everything about the shoe smells and feels like quality. The Wingtip Brogue upper is made out of a premium full-grain leather, and the insides also the lux treatment as well. The lining is leather, and so is the surface of the foam-backed insole – all which make the interiors super smooth and comfortable.

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

A word of caution about the upper fit – the sizing fits at least a full-size large for both the Derby (featured) and Wingtip Brogue versions.

Also see: Ecco ST1 Hybrid Brogue Oxford, a dressier variant based on the same midsole.

6) Ecco Seattle Tie

Ecco shoes tend to run expensive, but the Seattle tie does not. This dress shoe packs a lot of value for its $130 MSRP. Take, for example, the full-grain leather upper styled in a Derby silhouette. Or the functional comfort provided by the leather-lined insole and a full-length Polyurethane midsole.

Its clean, apron design puts in the formal wear category but without being as dressy as Wingtip brogues. The upper is mesh-lined instead of leather which gives it good moisture-wicking properties. Unlike the ST.1 Hybrid models, the Ecco Seattle Tie fits true to size.

Also see: The Florsheim Midtown Moc Toe has a similar silhouette and pricing as the Ecco Seattle. It features a cushy Ortholite footbed along with a rubber sole and suede-lined interiors.

7) Florsheim Midtown plain toe Oxford

We briefly mentioned the faux-Moc version of the midtown above. The plain toe Oxford is another variant based on the same fit and midsole but with a classic upper design that fits into most formal settings.

There’s plenty of room inside the leather-lined forefoot and toe-box so try before you buy – you might have to size down. The premium leather upper doesn’t require a break-in period; the Ortholite and rubber sole provides plenty of all-day comfort.

8) Johnston and Murphy XC4 Elkins Wingtip – Waterproof

The J&M Elkins Wingtip is a waterproof dress shoe with a comfortable insole that can be replaced with an aftermarket orthotic. The upper interiors are lined with mesh and sheepskin for a smooth over-the-foot feel.

The midsole and outsole use a combination of a heel foam core and rubber for cushioning and traction.

Also see: J&M XC4 Elkins Plain toe

9) Johnston and Murphy XC 4 Branning Moc Toe – Waterproof

The XC4 Branning Moc Toe’s apron design has a versatile dress shoe aesthetic that suits most occasions. The waterproof upper makes it an all-weather dress shoe.

If you’re into horology, think of the Branning Moc Toe as the equivalent of a complication-free dress watch with a black dial – classy enough to go with a formal attire while being equally at home when worn with a Polo and Khakis.

The sheepskin and mesh lining keeps the interiors soft. The memory foam insole adds soft step-in comfort; the heeled rubber midsole adds a dress shoe aesthetic while being comfortable.

Also see: The Johnston and Murphy Branning Cap Toe.

10) Mephisto Marlon

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

The plain toe Derby design isn’t the dressiest shoe silhouette but will work for most formal and semi-formal environments.

The Mephisto Marlon’s fit runs large, so you need to buy a smaller size than your regular fit.

11) Rockport Total Motion Sports Dress Wingtip

By marrying a very dressy leather upper with a sneaker-like midsole, the Rockport Total Motion Dress Wingtip channels its inner Cole Haan. A TPU shank provides the same support levels of traditional metal shanks without setting off airport metal detectors.

The molded insole padding and the foam midsole makes the ride very comfortable. The fit is large, so you’re better off ordering a half size smaller.

A contrast color midsole makes it the most ‘casual’ dress shoe on this list.

12) Rockport Big Bucks Margin

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

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