The Most Comfortable Men’s Dress Shoes

A pair of good dress shoes can elevate your regular office attire to a whole new level in terms of both style and comfort. So why is it that so many men struggle to find a good pair of smart brogues? The fact is, many times, people don’t wear in their shoes for long enough, or they pick a pair that don’t fit properly. To help you avoid these common pitfalls, this buyer’s guide compiles some of the most comfortable men’s dress shoes available, from comfortable double-monk straps to stylish brogue oxfords, along with some Q & A’s to help you decide what’s best for you.

Sure, dress shoes are not what’s always called for, and that’s why we’ve also covered the most comfortable work boots for men, but in this guide, we’re going to focus on dress shoes that won’t leave your feet tired, sweaty and aching at the end of the day.

What are the most comfortable men’s dress shoes?

The most comfortable men’s dress shoes on this list are the stellar Beckett Simonon Dean Oxfords, an Italian-made pair of oxfords with a high-quality build and a range of comfort-friendly features. The Deans are stitched with a Vachetta leather lining crafted to regulate your feet’ temperature and wick moisture away from them. They also have a large instep volume and rubber soles that redirect pressure away from your feet, preventing aches and pains in your joints. The leather-lined insoles will gradually adjust to the shape of your foot, so after a week or so of wearing, you’ll have a perfectly fitted shoe that feels soft to the touch.

What is the brand of most comfortable men’s dress shoes?

One brand that stands apart in the world of comfortable dress shoes is Cole Haan. They have a wide range of classic and casual shoes, often blending modern materials with time-tested styles for a variety of good-looking, hard-wearing products. The UltraGrands is a sporty blend of a sneaker-like sole and stitched brogue suede, while the Zergorands lean into a classic look with a super-thick, super-comfortable sole. And if you’re after something more traditional, Cole Haan’s Lewis Grand 2.0s are a straight wingtip oxford shoe with a thick shock-absorbing sole and a soft leather upper.

What are the best dress shoes for standing all day?

If you ever do a deep dive on the publicly available reviews for the most comfortable men’s dress shoes, you’ll see the brand Allen Edmonds praised wherever you go. They’ve been making high-quality shoes for decades, and though the price of entry is a little higher, it’s hard to beat the Allen Edmonds Strandmok oxfords in terms of quality and comfort. Built to keep you going all day long, the Strandmoks has a cushioned, leather-covered footbed and an Italian suede upper designed to reduce chafing around the ankle arch. This makes them a great pick for office and casual wear alike.

Why are men’s dress shoes uncomfortable?

The thing about dress shoes is that there’s nothing that makes them inherently uncomfortable. Most people face the major issue because they choose shoes that are too thin for their feet without realizing it, or they fail to wear them in properly and give up before they do so. Dress shoes are stiff at first if they’re made of leather, but with time, this stiffness slowly gives way to a supple, soft build that perfectly matches the shape of your foot.

If your dress shoes still aren’t comfortable, even once you’ve found the right size and worn them in, you can always experiment with different thicknesses of socks or various insoles to improve the feeling of the shoe. Everybody’s feet are different, and you have to find what works for you. 

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1. Cole Haan OriginalGrand Ultra Wingtip Oxford

The Cole Haan OriginalGrand Ultras are comfortable casual men’s dress shoes with a wingtip oxford style, pairing a mix of high-quality leather and synthetic rubber for a sturdy, sporty dress shoe. Available in 15 different styles, the OriginalGrand can be customized for any wearer, with options ranging from suede finishes to premium leather to stitched canvas. With a soft cushioned construction, every option is guaranteed to be comfortable to wear.

2. Allen Edmonds Strandmok Dress Shoes

It can be hard to find comfortable dress shoes for wide feet, but Allen Edmonds has considerately offered up a variety of wide sizes with their Strandmok range, making for great dress shoes that anybody can wear. These shoes also have a breathable leather lining and a detailed oxford style with classic brogue detailing on the toe cap, making them stylish to boot. Allen Edmonds are renowned for their comfortable, high-quality shoes, so these are my personal top pick.

3. La Milano Double Monk Loafer

A double monk strap is a nice alternative to a laced construction when choosing hard-wearing and comfortable dress shoes for men. The La Milano Double Monk loafers aren’t just practical but also supremely stylish. These lovely shoes come in five colorways, including a burnished burgundy and a rich, tanned cognac brown. This is a classic, comfortable slip-on shoe perfect for any occasion.

4. Beckett Simonon Dean Oxfords

The Dean oxfords from Beckett Simonon are a minimalist pair of stylish men’s dress shoes constructed from some of the highest quality materials available. These shoes have an Italian full-grain leather upper that will build up a beautiful patina over time, making for a bespoke product that only improves with age. Blake method stitching has been used to secure the soles to the leather, all by hand, meaning they’ll last you for years without degrading – and should they eventually begin to fail, they’ll be easy to get resoled at a low price.

5. Clarks UnKenneth Way Oxford shoes

Clarks’ UnKenneth Way loafers are a pair of comfortable dress shoes for work environments specifically. They’ve added extra padding in the collar and tongue to create an incredibly soft and easy-wearing pair of loafers, built to prevent wear on your ankles even after a long day of walking between meetings. These shoes come in brown or black leather and sport a minimalist, understated loafer style, with sturdy rubber soles.

6. Ecco Citytray Plain Toe Tie Oxfords

If simplicity and comfort are what you look for in a good shoe, then the Ecco Citytray Plain Toe derby is the best choice for you. A derby shoe gives a looser tie than a tight oxford, giving it an overall flexible construction that’s ideal in a comfortable dress shoe. While these aren’t the flashiest pick on this list, they’re great at what they do, and their simplicity means they work for any occasion.

7. Ace Marks Wholecut Oxford

These whole-cut oxfords from Ace Marks sport an Italian calfskin leather upper with waxed dress shoe laces and an expertly-applied lower burnish. This gives the shoes a lovely two-tone effect sure to develop beautifully with age – but they’re not just good to look at. They’re also supremely comfortable, all thanks to their calfskin leather lining and flexible construction. Plus, they’re fully resoleable, making them an ethical and practical choice that’ll last you decades to come.

8. Cole Haan Zerogrand Oxford

Cole Haan’s Zerogrands differ from their UltraGrands in a few key areas, including a low-top ankle arch and an EVA polymer midsole bolstered by a rubber outsole. These shoes are cushioned for supreme comfort and available in various styles, with a range of leather and suede upper options. The ultra-thick soles give them a distinctive look, making them a good pair of casual dress shoes for both work and play.

9. Mephisto Cap Vert Loafers

The Mephisto Cap Vert is a stylish slip-on loafer that’s been padded around the collar and tongue to make it one of the most comfortable men’s dress shoes going. It’s water-resistant, too, making this pair a great choice no matter what the weather brings, and their soles are made from Caoutchouc rubber, a natural, non-vulcanized rubber that gives a soft and gentle tread. While they may not last as long as more durable dress shoes, these are perfect for the occasional city jaunt or for wearing indoors.

10. Dr. Scholl’s Shoes Sync Oxford

Available in six styles ranging from smooth black leather to grey striped wool, Dr. Scholl’s Shoes’ Sync oxfords are an interesting blend of the old and the new. Though built in a classic style, these shoes use only modern materials, with a faux-leather upper, synthetic rubber sole, and Lycra comfort collar. The Syncs are built as casual men’s dress shoes, focussing on style and comfort, and their extra toe and heel support makes them ideal for everyday use.

11. Mephisto Marlon Oxford

Pebble grain leather shoes are quite hard to find, so the Marlon oxfords from Mephisto are something of a rarity. Their outer style isn’t the only thing unique about them. However, they also utilize sophisticated Air-Jet circulation midsoles to ensure that your feet aren’t just dry and cool and comfortable all day long. Available in three striking colorways, these are an alternative, eye-catching choice.

12. Ecco Seattle Apron Toe Oxford

The Ecco Seattle Apron Toe oxfords are something of a blend between styles, with a derby throat, an oxford tie, and a loafer silhouette. These features combine for a shoe that’s built for comfort, with a highly breathable textile lining and a comfortable insole designed to increase air circulation. The soles are engineered to reduce the pressure on your ankles and knees when walking, and a 100% leather upper will keep you dry in the rain too. Overall, these shoes are a sturdy pair of all-rounders.

13. Rockport Tanner Wing Tip

The classics are often the best, and Rockport’s Tanner wingtip oxfords prove this idiom once again. A comfortable and stylish men’s dress shoe, they contain a breathable lining and a cushioned footbed for supreme support and moisture-wicking. They’re made from full-grain leather with durable rubber outsoles, and have a restrained brogue embossing on their toe caps, making them great comfortable dress shoes for work.

14. Johnston & Murphy Bradford Oxford

These Indian-made shoes combine various high-quality materials to make a durable pair of men’s comfortable dress shoes. These are similar to many of the oxfords we’ve seen before, but what sets the Bradfords apart is their lovely brushed finish. This gives the shoes a smooth sheen and a smart look, and the minimalist brogue detailing completes the package for a subtle but striking pair of shoes.

15. Vionic Shane Lace Up

These comfortable dress shoes for work from Vionic combine a classic derby style with enhanced orthotic technology for a supportive shoe built to reduce aches and pains during everyday use. With FMT comfort technology built into the design, and a refined, tailored silhouette, the Shane lace-ups are a great combination of both function and form, available in two lovely high-sheen colorways.

16. Clarks Atticus Cap Oxford Shoes

Available in either navy nubuck suede or genuine tanned leather, the Clark Atticus Caps are a breathable pair of dress shoes built for casual, everyday wear. They have a classic welted sole with a low heel and a gentle ankle arch, resulting in a low-profile pair of shoes perfect for wearing out on the town or inside the office. These are great multi-occasion shoes with a fairly comfortable build.

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