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 November 2023. The SAS Ambassador is a new addition.

Santoni Leather Heel

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

This guide isn’t about dress shoes with an all-leather construction and a Blake-stitched sole. It’s about comfortable office shoes that combine old-school traditionalism with cushioning from the athletic footwear industry.

We’ve curated nearly a dozen models from the hundreds of available options using the following filters.

Florsheim with Cole Haan Zerogrand dress shoes

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

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.

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.

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. Many shoes on this guide – like the Florsheim Midtown and SAS Ambassador – have folded tongue edges.

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 a couple of models, 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.

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. We have a separate guide for waterproof dress footwear.

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.

The Ecco ST1 Hybrid Gore-Tex in the rain.

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.

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; our review explains more.

3) Ecco CityTray Gore-Tex Waterproof

From the outside, it’s hard to tell that the Ecco CityTray GTX 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) Ecco Metropole London Wingtip

The Ecco Metropole London is a new intro by the Scandinavian brand that nails down the traditional Wingtip Derby aesthetic – right down to the block heel and welted upper.

From the outside, it looks very much like an old-school Derby, except that the shoe has a few modern upgrades. The upper is Goodyear-welted to a cushioned Polyurethane (Phorene) midsole that makes everyday wear very comfortable.

There are other comfort-oriented features too. The leather-lined footbed is padded for step-in softness. Ecco also takes a leaf out of Johnston’s and Murphy’s playbook and makes the insole ‘dual-fit.’ What this means is – removing the insole reveals another footbed (non-removable), so it’s possible to open a lot more room by removing the insole. That makes the Metropole a sensible choice for wide feet.

The soft leather upper uses a folded tongue for instep comfort, and the waxed laces complete the dress 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) Johnston & Murphy Jameson Longwing

Johnston & Murphy has a made-in-Italy line with a higher quality of materials and finish; the Jameson Longwing is one of them. Here, the Longwing refers to the Wingtip panel that extends to the heel. On the standard Wingtip shoes, the panel stops short of the midfoot.

And why is the shoe on this guide? Rather than a block leather sole, the Jameson is Goodyear-welted over a lightweight EVA foam midsole. There’s no separate outsole, so that helps keep the weight down.

Inside the shoe is a padded and leather-lined footbed; even the upper is lined with leather for a smooth interior. The Jameson is from J&M’s higher-tier assortment, so the leather is more premium with an applied burnished effect.

10) (Made in USA) SAS Ambassador

While brands like Allen Edmonds and many small-batch manufacturers sell US-made dress shoes, SAS (San Antonio Shoemakers) are the only folks who make their their assortment in the United States.

The SAS Ambassador uses a traditional Derby leather upper over a lightweight Polyurethane sole. The leather-lined footbed adds soft and non-irritating step-in comfort.

The leather upper makes the interiors comfortable, as it combines soft materials with a folded tongue flap and padded heel. The leather is heavily corrected, so it’s not exactly high-grade.

The overall build quality is solid and comparable to the Florsheim Midtown, except that the Ambassador’s high price reflects the cost of producing domestically. But there’s one area where the SAS Ambassador outperforms all others on this list – the upper is available in four widths.

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