In this product guide:
- 1. Our top pick: Florsheim Midtown Cap Toe
- 2. Ecco ST.1 Hybrid Brogue Tie
- 3. Ecco Citytray Gore-Tex
- 4. Cole Haan Originalgrand Wingtip
- 5. Ecco London Metropole Wingtip
- 6. Cole Haan Remastered 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
There are three reasons why the Florsheim Midtown is our top pick in this guide.
First, it looks like a proper dress shoe. The design doesn’t overdo the ‘sneaker hybrid’ aesthetic that is now commonplace. The Midtown is available in two versions – cap-toe or plain-toe upper. The faux welt detailing and block heel is strongly inspired by traditional dress shoes.
Two, the Florsheim Midtown is extremely comfortable. A soft, leather-covered footbed adds step-in softness closer to the foot. The synthetic rubber outsole makes walking and standing comfortable; it also grips much better than a conventional leather sole.
While the upper is made of leather, there’s plenty of interior comfort. The soft suede lining increases comfort, and so does the padded tongue. The fit isn’t too narrow, so there’s plenty of toe-box room. The athletic footwear construction also keeps the weight low. The Midtown is the only shoe in this guide to be sold in multiple widths.
Last but not least, the Florsheim Midtown is a comfortable dress shoe at a reasonable price. While it’s priced at $125, it can often be had for under $100. It’s excellent value for a dress shoe that punches above its price class – it looks and fits like a shoe that’s twice as expensive.
If you’re willing to pay more for extra comfort, support, and durability, then the Ecco ST.1 Hybrid is a no-brainer. We’ve had this shoe for over four years now, and we love its everyday versatility and comfort. There’s barely any wear on the grippy outsole too.
Most Ecco shoes use Polyurethane (PU) foam – a material that offers an excellent blend of comfort, stability, and durability. The ST1. Hybrid uses a 100% PU midsole with a leather-covered footbed on top. With this setup, the plushest part of the midsole is the closest to the foot.
The upper is available in three variants. There’s the plain toe version, a brogue design, and another with a faux cap toe. Regardless of the version, you’ll get a comfortable upper made with premium-looking leather. The supple leather upper and lining make the interiors smooth and secure. The upper has a snug fit, so try before buying, if possible.
Except for the thick midsole, the all-black ST1.Hybrid has strong dress shoe aesthetics.
The availability of the Gore-Tex version is spotty, so grab them when you can. The waterproof variant uses the same midsole and outsole as the standard model, so you’ll get the same level of comfort.
- Ecco’s marketing pitch: Feel and comfort of a sneaker.
- Upper: Leather with textile lining, Goodyear welt.
- Upper fit: True-to-size with snug fit.
- Midsole: Phorene Polyurethane foam with a softer heel core.
- Outsole: Single-piece thermoplastic rubber.
- Weight: 481 gms/ 1 LB 1 Oz for a half pair of Men’s US 9/UK 8/EUR 42.5/CM 27.
- Available widths: D – regular (reviewed), 2E – wide.
- Country of origin: Portugal.
- Airport friendly?: Partially – has metal eyelets.
- Recommended use: Daily commute, walking, standing all day.
- Median lifespan: 800 miles.
- Recommended temperature range: Warmer than -5° C/23° F.
Pros
- High level of comfort
- Very stable ride
- Plush leather-covered insole
- High midsole and outsole durability
- Well-proportioned upper fit
- Goodyear welt adds dressy touch
Cons
- Heavy
- Lack of widths
- Downmarket laces
- Poor grip on slushy sidewalks
- Upper heel fit
If you like the comfort of an Ecco shoe but want a sleek and lightweight dress shoe, consider the Citytray. It’s sold in two versions, regular and waterproof. Regardless of which variant you buy, both shoes offer equal comfort.
The leather-topped insole offers plush underfoot padding for all-day comfort. The heeled Polyurethane foam sole resembles a traditional leather sole, but provides superior traction and cushioning without adding bulk.
Ecco opts for a simple and uncluttered upper design. The Citytray is available in just a plain-toe upper, but in two variants – standard, and a waterproof Gore-Tex version. Both versions use the same sleek European last (form), giving the shoe a streamlined aesthetic.
Cole Haan created the modern dress sneaker category, and the Originalgrand (earlier called the Lunargrand) was the first of its kind. The 2025 Originalgrand combines a brogue wingtip leather upper with an EVA midsole for dressy comfort.
The EVA midsole adds plenty of lightweight padding under the foot. The outsole rubber is applied selectively to increase softness while keeping the weight low. A textile-covered foam insole is placed closer to the foot for step-in comfort.
On the upper, the leather and fabric lining make the interior comfortable.
Are there any downsides to owning the Originalgrand? While the shoe delivers modern-day comfort in an office-worthy design, the upper uses heavily corrected (lower quality) leather. It also fits tighter than comparable dress hybrid shoes.
From the outside, the Ecco Metropolitan London looks like a traditional Derby with a Wingtip toe. The burnished leather upper, brogue detailing, block heel, and true welts are bonafide dress shoe elements.
It’s only when you wear the shoe where things get interesting – or shall we say, more comfortable. The Metropolitan London offers excellent everyday comfort, courtesy of modern material and design upgrades.
The Polyurethane (Phorene PU) foam midsole adds supportive cushioning and grip; the leather upper is padded in the heel and tongue for comfort. The tongue flap has folded edges to avoid irritating the top of the foot.
The insole is ‘dual width’, meaning it can be removed to make the fit more spacious. Removing the insole reveals a second footbed (non-removable), which also makes inserting an aftermarket orthotic possible. If you have wide feet, the Metropole London makes a strong case for itself.
The ZeroGrand Wingtip is the closest one gets to a running shoe, simply because it is directly inspired by one. The ultra-flexible foam midsole is based on the Nike Free, a running shoe with extra-deep grooves.
Thanks to its flex grooves, the Zerogrand is lighter and more flexible than most dress hybrids. The FlowerFoam EVA midsole and soft insole add everyday comfort to office commutes.
The ‘remastered’ edition offers two things the previous version did not. The upper has more room around the toes, and the midsole gets a full-length rubber outsole for better grip and durability. The heavily-corrected leather is still very average, so the Zerogrand isn’t great value at full retail price.
While the running shoe-inspired midsole tones down the dressiness, the Zerogrand still fits into an office environment with its laser-etched Brogue details and the five-eyelet lacing system.
The J & M Melton Cap Toe is the only shoe in this guide with a leather sole, so you won’t get dress sneaker levels of comfort. That being said, the smooth leather-lined upper, foam footbed, and half-rubber heel makes the shoe more comfortable than a traditional dress shoe.
Even though the leather sole uses genuine Goodyear-welt construction, the thin sole is lightweight and flexible for comfort.
The rest of the shoe is based on a traditional cap-toe Oxford silhouette constructed with modern materials. The fine stitching details on the cap-toe and quarter panels elevate the aesthetic appeal, and so do the black tipped edges.
SAS (San Antonio Shoemakers) is one of the last remaining brands to make 100% of their shoes in the USA. Other companies like Allen Edmonds make some, but not all, of their shoes Stateside. The US-made SAS Ambassador is priced close to $300, reflecting the cost of domestic production.
SAS relies on the tried-and-tested dress-hybrid playbook to make the shoe comfortable. The footbed and midsole are made of Polyurethane (PU) foam to make commuting and all-day wear comfortable. The absence of a rubber outsole keeps the weight low.
The Ambassador improves traditional Derby design by adding a padded heel and tongue for interior comfort. As a bonus, the shoe is sold in multiple widths, ranging from a B (narrow) to a 4E (extra-wide).
A retail price doesn’t necessarily get you high-end materials. While the upper is soft and durable, it is made of heavily corrected leather that is usually found in entry-level footwear.
The upper plays it safe with the conservative upper and midsole design, making the cushioned SAS Ambassador dressy enough for office wear.
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.
Here’s another example. The pictures you see below are of Santoni’s Limited Edition – shoes that retail for $2,000, making them one of the most expensive dress shoes in the industry. The LE models are leagues above Santoni’s ‘Nordstrom’ line-up.
Naturally, at this price, you get the works. Lots of hand-finished detail, hand-painted leather, closed channel Goodyear Welt, and reverse stitching. Heck, it even comes boxed with a Santoni Brush and premium metal shoe horn.
Despite being at the top end of the dress shoe hierarchy, the Santoni LE is anything but easy on the feet.
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 recommended luxury footwear brand) 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.