Most Comfortable Dress Shoes for Men

by Solereview editors
Published: Last Updated on

The Most Comfortable dress shoes for men 2021

This article has been updated with current models for April 2023. The Clarks Un Tailor Tie and Cole Haan Grand Ambition have been removed. Most of the shoes were purchased at full retail price.

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

Several shoes on this list will pass muster as ‘proper’ dress footwear. The Florsheim Midtown, Ecco ST.1 Hybrid, and Rockport BB Margin are good examples.

On the other hand, shoes like the Cole Haan OriginalGrand Wingtip and Johnston & Murphy Holden are dress sneakers that work better on casual Fridays rather than pleated trousers cut of super-130s cloth. Perhaps ‘officewear’ is a fitting description of such 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. The difference in comfort is stark when compared 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 a traditional 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.

Even the rubber soles used on British dress shoes – like the popular 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.

Santoni Leather Heel

The stacked leather heel of a typical dress shoe. These are hard and lack ride comfort.

Santoni Goodyear Flex Leather Sole

Leather soles also grip poorly over smooth surfaces. Like tiled floors, for example.

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 Cole Haan Grand Ambition Wingtip Oxford on the sidewalk

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.

Florsheim with Cole Haan Zerogrand dress shoes

Pictured here: The Florsheim midtown with its Ortholite footbed, and the Cole Haan Zero Grand Wingtip.

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 weight.

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

The EVA sole of the Clarks Un Tailor Tie.

The midsole has a traditional look, but it’s made of lightweight EVA foam for comfort.

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

The removable Ortholite insole of the Clarks Un Tailor Tie.

Look for a cushioned insole with arch support. Pictured here is the Ortholite insole from a Clarks shoe.

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.

The removable insole of the Ecco ST1 Hybrid Gore-Tex.

The leather lining enhances the footbed comfort.

4) Leather uppers in a traditional silhouette: That’s because mesh shoes stray into the casual shoe category.

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.

The folded tongue edges of the Florsheim Midtown.

A folded tongue flap is comfortable and needs no time to break in.

6) Safe colors: If you thought that the colors on this guide are boring, it’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 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. The only exception is the John Lobb City II, which has a Goodyear-welted EVA sole on an Oxford upper.

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 City Tray Gore-Tex is waterproof.

Side view of the Ecco ST1 Hybrid Gore-Tex.

Some shoes – like the Ecco ST1 Hybrid – have Gore-Tex inside.

This guide contains various dress shoe silhouettes, so here’s a quick style primer. A Wingtip 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 Florsheim or 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 Ecco ST.1 Hybrid. 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. We purchased the shoes at full retail price for our reviews.

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, and also follows all the best practices that make a dress shoe comfortable.

The rubber heel of the Florsheim Midtown.

The Midtown uses a traditionally-designed TPR (rubber) sole.

The leather footbed of the Florsheim Midtown.

The removable insole is extremely comfortable. A leather footbed covers the dual-density foam insole.

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 padded heel lining of the Florsheim Midtown.

The ‘Suedetech’ lining used inside the upper is superlative. It even has a slight foam padding for extra 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 Florsheim Midtown on the road.

The light reflects on the leather revealing different shades of brown.

The Midtown Cap Toe, along with the Ecco ST1 Hybrid, 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) Ecco ST1 Hybrid Wingtip

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.

The TPR outsole of the Ecco ST1 Hybrid Gore-Tex.

The ST1 Hybrid has a dual-density Polyurethane midsole with a soft heel core.

The shock absorbing core of the Ecco ST1 Hybrid Gore-Tex.

During walking, the heel is cushioned by the soft PU foam plug.

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 is an excellent waterproof dress shoe. The GTX and standard ST.1 Hybrid share the same midsole and footbed, so our review contains plenty of relevant information.

(Tester’s note: We have owned the ST1 Hybrid for over two years, and it has proved itself to be a versatile dress substitute. At the one year mark, there was minor delamination of the midsole and outsole near the tip. Ecco honored the warranty and replaced it for no charge.

Ecco has also released a new model called the ‘Lite Hybrid Brogue’. It has a similar upper as the ST.1 Hybrid, but without the welt over a new midsole design. This guide will be updated with more information once we buy and test them.)

3) Ecco CityTray Gore-Tex Waterproof

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.

4) 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.

5) Cole Haan OriginalGrand ShortWing

Cole Haan is the creator of the modern ‘athletic fusion’ category, and the OriginalGrand silhouette is its most vocal advocate. Our detailed review of this dress sneaker is here.

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.

The molded insole of the Cole Haan Originalgrand_Wingtip.

The removable insole has a contoured EVA frame to cup the foot.

The outsole rubber of the Cole Haan Originalgrand_Wingtip.

Only the heel and forefoot have outsole rubber inserts.

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.

The midsole of the Cole Haan Originalgrand Wingtip Oxford.

The Cole Haan Originalgrand’s midsole is inspired by the Nike Lunaracer.

6) Rockport Garett 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 allow the Garett to 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.

7) 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.

The outsole of the Cole Haan Zerogrand Wingtip Oxford

The Nike Free influence is easy to spot here. Notice the soft core inside the midsole.

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.

8) 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 removable footbed of the Johnston and Murphy Holden Wingtip

The Holden’s three-layer insole is very comfortable and supportive.

The memory foam insole of the Johnston and Murphy Holden Wingtip

The Holden’s insole has three layers – a memory foam fill between a Sheepskin footbed and an EVA foam frame.

The midsole and outsole are part of a foam mono-sole 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.

The decorative welts of the Johnston and Murphy Holden Wingtip

The ‘welts’ on the midsole are decorative.

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.

9) 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.

10) John Lobb City II New Standard

There’s just one luxury dress shoe on this guide, and that would be the John Lobb City II on an EVA foam sole. (Another City II variant on a leather sole also exists.)

Not many people know that the John Lobb brand (Paris) is owned by Hermes – yes, the same Hermes of the Birkin handbag fame.

Hermes’s forte is leather craftsmanship, so that’s what you get with the John Lobb City II. Large panels of supple Calfskin are stitched together in an elegant Oxford-style upper.

A leather-covered footbed and calf-skin lining make the interiors very smooth.

The nice upper aside, the lightweight EVA foam walking sole is the real reason why the JL City II New Standard is featured here. It’s an unusual kind too – the foam sole is Goodyear-welted to the upper. That gives the City II the aesthetic of a formal shoe, but without the harsh ride.

(Note: Hermes owns the John Lobb ‘Paris’ brand. The John Lobb on Regent Street, London, is an independent entity.)

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