Top 10 Most Comfortable Dress Shoes For Men

1. Beckett Simonon Dean [Oxford Shoe]

If you’re not particularly fond of high-tech materials and modern concepts, we highly recommend Beckett Simonon as a worthwhile alternative. Benchmade in Colombia, these men’s dress shoes manufactured from Gold Standard full-grain Italian leather with a traditional Blake stitch construction.

Admittedly, we struggled to choose a favourite model. However, like the Wolf & Shepherd Closer above, the “Dean” is another timeless cap toe Oxford that will be incredibly versatile whatever your needs. And with our 20% discount code “BU20“, a pair costs the same as Cole Haan dress shoes!

Although Goodyear welting is often seen as the pinnacle of craftsmanship, there is much to be said for the Blake stitch. Firstly, a Blake stitch breaks in much faster than Goodyear welt, so it’s more comfortable to wear right out of the box.

Additionally, it’s more flexible and often lighter to wear than a bulky Goodyear-welted shoe. Beckett Simonon also uses chromium-free vegetable-tanned wholecut linings in their shoes. Therefore, you don’t experience any chafing on the stitch work. Therefore, they’re an impeccable choice when on a budget.

2. Ace Marks Vincent [Brogue Shoe]

If you’re looking for a more outgoing style, Ace Mark’s Italian-made Vincent was our favourite model from the brand that provided the most comfort. Thanks to a Blake Flex construction, these men’s dress shoes offer added flexibility, which heightens the comfort.

Similarly, they’re crafted from supple calfskin leather uppers, which moulds to the wearer’s feet over time. Combining impeccable style with traditional Italian craftsmanship, these are certainly worth your attention.

If you’re not fond of the burgundy and tan full-grain leather upper combination, there are plenty of other colourways available through their site linked above.

3. Amberjack The Original [Derby Shoe]

While Amberjack’s The Original isn’t a dress shoe in the traditional sense, times are changing and business casual is becoming more common in settings that formerly commanded strict dress codes.

Amberjack’s founder, John Peters, sought to create a versatile shoe brand that produces affordable yet comfortable footwear. To achieve this, he teamed up with designer John Kraljevich who has worked with brands including Allen Edmonds, Coach, and John Varvatos. You can learn more about its full story with our review.

The resulting flagship model, The Original, is a hybrid that marries traditional craftsmanship with modern athletic footwear technology. Its footbed is three times thicker than those from similar brands and features heat-activated arch support. Meanwhile, the lightweight outsole provides both stability and traction while the supple American cowhide uppers offer excellent comfort. Most recently, the brand has also introduced Chelsea boot styles employing the same comfort-imparting technology.

Conclusively, the comfort, styling, and value for money have earned The Original a well-deserved spot on our list.

4. Wolf & Shepherd Longwing [Hybrid Shoe]

Wolf & Shepherd is a premium brand that produces some of the world’s most comfortable dress shoes for men. If you’re like us, you may be somewhat skeptical of all the hype. However, we have tried a number of their shoes ourselves and can now attest to how the memory foam may earn you all-day comfort!

By melding calfskin leather uppers with high-density TPU soles, they’ve managed to bring a modern element to classic styles. Additionally, as they’re quite light, you won’t experience fatigue even when wearing them for extended periods of time. Ultimately, at this price point, they’re one of the most comfortable men’s dress shoes we’ve come across.

Lastly, if the brand name sounds familiar, it’s because their Crossover lines of shoes, including these Longwings, have garnered quite a bit of traction online as well as in the mainstream.

5. Allen Edmonds Strandmok [Brogue Shoe]

Interestingly, the Allen Edmonds Strandmok is one of the first pairs of men’s dress shoes that we reviewed on Bespoke Unit. After all this time, it still remains one of our favourite pairs and easily outperforms many newcomers.

Although crafted with the Allen Edmonds 360° Goodyear welt, they’re flexible and offer a pleasant stride. This is partly thanks to the striking Dainite rubber sole that provide excellent shock absorption.

The Allen Edmonds Strandmok is available in a variety of styles with some more formal than others. However, we’re great fans of the distressed brown, which is made from a supple calfskin leather upper. As a wingtip Oxford brogue shoe, it’s less formal than a cap toe Oxford. Nevertheless, it should be fine in some offices.

6. Idrese [Custom Shoes]

Manufactured in Almansa, Spain, Idrese produces Goodyear-welted men’s dress shoes for less than $300. Furthermore, they’re custom shoes, which means that you can design them yourself using its website’s interactive tool! Many styles are available from wingtip Oxford dress shoes to a cap toe monk strap. The choice is yours!

We’re impressed by both the quality and value Idrese provides. However, we were particularly surprised by the comfort of its shoes, too. Indeed, Paul Anthony, Bespokes Unit’s founder, often struggles to find shoes that fit.

Fortunately, Idrese has a vast selection of sizes and widths. Paul was able to order his shoes in 14EEE and he was amazed by the comfort that they provided them. Finally, you can also choose between leather and rubber soles depending on the shock absorption you want.

7. Lethato [Kiltie Loafer]

Not only does Lethato’s kiltie slip-on loafers feature an unusual and original design, but they’re also made in India! Indeed, Lethato is a proudly Indian up-and-coming dress shoe brand that offers hand-painted footwear at excitingly tempting prices.

Its price points vary depending on whether you opt for Goodyear-welted and Blake-stitched shoes. In the case of the kiltie slip ons, they feature a Blake stitch. The unique design combines a monk strap, a kiltie vamp, and wingtip broguing. It may not be to everyone’s taste, but it certainly stands out!

A cushioned footbed offers comfortable support and rubber outsole provide additional grip. Admittedly, the loafers aren’t incredibly comfortable out of the box. Indeed, they have a tendency to briefly pinch as the last has a different shape. However, within just a day, they will have broken in to provide as much comfort as any of the other dress shoes listed here.

8. Beckett Simonon Lopez [Formal Boot]

Chukka boots are often very casual in appearance compared to a typical dress shoe. Yet, Beckett Simonon has successfully redefined the style to offer a more premium and elegant aesthetic. The result is the Lopez, which is a low ankle-length boot made with a Gold Standard Italian calfskin leather upper.

Inspired by the boot’s First World War heritage, it offers style and function. Like the Dean Oxford shoes, the Lopez features a Vachetta leather lining, which is smooth and comfortable. Furthermore, the rubber sole provides comfortable shock absorption.

9. Mephisto Cap Vert [Loafer]

Although we appreciate Mephisto’s quality, we tend to avoid its men’s dress shoes as they’re not particularly attractive. However, the Cap Vert is certainly an exception. As a spenny loafer, they’re a business casual option. Therefore, we wouldn’t pair them with a suit but they’re an excellent choice when being up on your feet all the time.

As slip-on loafers, they’re very convenient. Furthermore, extra padding in the tongue reduces pressure points.

Meanwhile, an extra soft leather lining is designed with a special Air-Relax cushioned insole for additional breathability. Therefore, they’re an excellent option in any season.

10. Ecco Citytray [Derby Shoe]

Ecco is a celebrated comfortable dress shoe brand. Often marketed as a cheaper alternative to Mephisto, its men’s dress shoes can occasionally be a little too utilitarian for dressy wear. As a result, people often just opt for Cole Haan instead. However, the Ecco Citytray is a wonderful exception.

Opting for a classic Derby design, it’s not quite as formal as some of the Oxford shoes featured elsewhere in this list. However, it’s understated and good enough for both office and catering work.

The insole is removable so you can use your own. Furthermore, it features lightweight Fluidform Comfort Technology soles. As the name suggests, it also uses Ecco’s Tray technology that provides additional stability and grip, which is perfect when on the move.

11. Rockport Tanner [Brogue Shoe]

If you’re on a strict budget, Rockport is a reliable dress shoe brand that you can trust. While Cole Haan or Johnston & Murphy dress shoes are typically chosen on this budget instead, Rockport has many benefits for comfort. The Tanner range offers some decent-looking wingtip Oxford shoes that you can easily wear for different occasions.

For instance, it features a removable OrthoLite footbed, which is a great brand of comfortable inserts. Meanwhile, its lightweight rubber outsole will help absorb shocks and provide you with extra grip.

Although not the best men’s dress shoes on this list, these wingtip Oxford dress shoes have earned their place thanks to both their price point and reliably.