In this product guide:
- 1. Our top pick: Florsheim Midtown Cap Toe
- 2. Ecco ST.1 Hybrid Brogue Tie
- 3. Waterproof dress shoe: Ecco CityTray Gore-Tex
- 4. Cole Haan Originalgrand Shortwing
- 5. Ecco London Metropole Wingtip
- 6. Cole Haan Zerogrand Oxford
- 7. Johnston & Murphy Melton Cap toe
- 8. SAS Ambassador (Made in the USA)
- 9. Our luxury pick: Ferragamo Tramezza Derby
- How we selected
The Florsheim midtown has a classic design that blends into most formal settings. It also follows all 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 Ecco ST1 Hybrid, is one of the dressiest shoes on this guide. Unlike modern dress sneakers, the dark-colored and heeled rubber sole has very traditional styling.
The plain toe Derby 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.
We’ve owned this shoe for over two years now, and the outsole looks just as new. At the one-year mark, the outsole began peeling under the toe, and Ecco replaced it without question. We haven’t faced that issue with the replacement pair since.
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.
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 the combination lining (mesh and leather) 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.
Cole Haan is the creator of the modern ‘athletic fusion’ category, and the OriginalGrand (earlier called the Lunargrand) was the first of its kind.
A leather upper in a wingtip brogue styling gives the Originalgrand all the dress-shoe legitimacy it needs. The decorative well on the edges is attached to a full-length foam midsole with a token placement of outsole rubber.
The EVA foam midsole offers 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.
Like most Cole Haan shoes, the Originalgrand has a narrow fit, so try before you buy.
The Scandinavian brand nails down the traditional Wingtip Derby aesthetic – right down to the block heel and welted upper.
From the outside, the Ecco Metropole resembles 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.
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 2024, 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.
Just watch out for the very narrow upper fit; the Zerogrand will likely not fit wide feet.
At the time of publishing this guide, Cole Haan seems to be updating this model with a ‘remastered’ Zerogrand, so watch this space for updates.
This is the only shoe on this list that doesn’t use a rubber sole. The Johnston & Murphy Melton also happens to be a Goodyear-welted dress shoe.
While it’s unfair to expect dress sneaker levels of comfort from this shoe, the Melton’s soft leather upper makes the interiors comfortable.
Directly under the foot is a leather-covered foam footbed that adds step-in comfort. The heel of the sole isn’t 100% leather. Like most modern dress shoes, the bottom layer of the heel stack is made of rubber for grip and comfort.
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 entire 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 durable but of inferior 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.
We saw this shoe being offered at a significant discount at a local store, so we bought it to prove a point – that even with the best materials and highest level of craftsmanship, a traditional dress shoe will be nowhere as comfortable as a dress sneaker hybrid.
The Ferragamo Tramezza’s premium leather upper and fit makes it more comfortable than a lower-tier GW dress shoe, but you get the idea.
And if you do end up buying a shoe that’s priced over $1000, we wanted to tell you what to look for.
Ferragamo has two shoe lines. There’s the regular (and cheaper) studio line found in many department stores, and then there’s the Tramezza collection. The latter is Ferragamo’s footwear line that is reportedly made by Paolo Scafora – the venerable Italian shoemaker.
This particular Tramezza Derby uses a soft Calfskin upper over a Goodyear-welted sole. The fit and finish is what you expect of a shoe that’s priced north of $1300. The quarter edges, tongue flap, and heel collar all have folded edges. The sleek upper hugs the arches and locks the heel in without folds on the top or the sides.
The footbed and lining is 100% leather, and all evidence of Goodyear welting is concealed under a closed channel that’s hand-painted over. The waist has a prominent bevel, and the upper has a two-tone burnished effect. While this derby is considerably less dressier than an all-black Oxford, other Tramezza shoe have similar fit and finish standards.
Now remember – this level of traditional shoe-making includes brands like John Lobb Paris, Gaziano and Girling, Bontoni, and higher end models from Santoni. Only brands like Berluti are priced higher.
Regardless of how comfortable the soft Calfskin upper is, these shoes are heavy and uncomfortable to walk around in. The multiple layers of leather on the sole add a lot of weight, and there’s no cushioning per se – with the exception of insole padding and cork fill.
If you want greater comfort, opt for Blake stitched sole over Goodyear Welt.
So if you want to buy a traditional dress shoe and want to avoid rubber soles, what should you do?
First of all, ditch the Goodyear sole and opt for a Blake construction instead. A blake-stitched shoe is more flexible, lighter, and is easier to break-in. That vastly increases comfort of a traditional dress shoe. The second suggestion would be to stick to brands that do insoles well. Santoni (pictured above) and Bontoni (Solereview’s preferred luxury footwear brands) are very comfortable and require the least amount of break in period.
How we selected: What to look for
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.
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 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.
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 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.
A folded tongue flap is comfortable and needs no time to break in.
6) Safe colors: If you think 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 which can easily cost north of $600. If you’re looking for an ultra-premium shoes, consider John Lobb, Paolo Scafora, and Salvatore Ferragamo (only their Tramezza lineup).
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.
9) Easy availability: We want our readers to try the shoe before buying, so we haven’t featured direct-to-consumer internet shoe brands.
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.